1999–2000 FA Cup qualifying rounds
The 1999–2000 FA Cup Qualifying Rounds opened the 119th season of competition in England for 'The Football Association Challenge Cup' (FA Cup), the world's oldest association football single knockout competition. A total of 558 clubs were accepted for the competition.
| Country |  England.svg.png.webp){kind=small} Wales |
|---|---|
← 1998–99 2000–01 → | |
The large number of clubs entering the tournament from lower down (Levels 5 through 9) in the English football pyramid meant that the competition started with five rounds of preliminary (1) and qualifying (4) knockouts for these non-League teams. The 32 winning teams from Fourth Round Qualifying progressed to the First Round Proper, where League teams tiered at Levels 3 and 4 entered the competition.
Calendar
| Round | Start Date | Matches | Clubs | New entries this round | Prize money |
|---|---|---|---|---|---|
| Preliminary Round | 21 August 1999 | 197 | 560 → 393 | 394: 187th–560th | £1,000 |
| First Round Qualifying | 4 September 1999 | 101 | 393 → 276 | 67: 182nd–186th | £2,250 |
| Second Round Qualifying | 18 September 1999 | 84 | 282 → 198 | 67: 115th–181th | £3,750 |
| Third Round Qualifying | 2 October 1999 | 42 | 198 → 156 | none | £5,000 |
| Fourth Round Qualifying | 16 October 1999 | 32 | 156 → 124 | 22: 93rd–114th | £10,000 |
| First Round Proper | 30 October 1999 | 40 | 124 → 84 | 48: 45th–92nd | £16,000 |
| Second Round Proper | 20 November 1999 | 20 | 84 → 64 | none | £24,000 |
| Third Round Proper | 11 December 1999 | 32 | 64 → 32 | 43: 2nd–44th | £40,000 |
| Fourth Round Proper | 8 January 2000 | 16 | 32 → 16 | none | £60,000 |
| Fifth Round Proper | 29 January 2000 | 8 | 16 → 8 | none | £120,000 |
| Sixth Round Proper | 19 February 2000 | 4 | 8 → 4 | none | £300,000 |
| Semi Finals | 2 April 2000 | 2 | 4 → 2 | none | £900,000 |
| Final | 20 May 2000 | 1 | 2 → 1 | none | £1,000,000 |
Manchester United, who were the winners the previous season, did not enter.
Preliminary round
Ties
| Tie | Home Team | Score | Away Team |
|---|---|---|---|
| 1 | A F C Totton | 1–2 | Weston Super Mare |
| 2 | Abingdon Town | 6–0 | Peacehaven & Telscombe |
| 3 | Accrington Stanley | 3–0 | Peterlee Newtown |
| 4 | Alfreton Town | 1–2 | Congleton Town |
| 5 | Arnold Town | 1–1 | Yaxley |
| 6 | Arundel | 1–2 | Portsmouth Royal Navy |
| 7 | Ash United | 1–2 | Chatham Town |
| 8 | Ashford Town (Kent) | 2–1 | East Preston |
| 9 | Ashford Town (Middx) | 1–2 | Langney Sports |
| 10 | Ashton United | 2–1 | Clitheroe |
| 11 | Atherton Collieries | 1–2 | Ramsbottom United |
| 12 | Aveley | 1–0 | Stansted |
| 13 | Backwell United | 5–1 | Andover |
| 14 | Bacup Borough | 2–2 | Sheffield |
| 15 | Baldock Town | 6–0 | Potton United |
| 16 | Banbury United | 2–0 | Milton Keynes City |
| 17 | Banstead Athletic | 0–2 | Thame United |
| 18 | Barwell | 1–1 | Staveley Miners Welfare |
| 19 | Bashley | 6–1 | Calne Town |
| 20 | Beaconsfield S Y C O B | 3–0 | Eynesbury Rovers |
| 21 | Bedfont | 4–0 | Tunbridge Wells |
| 22 | Belper Town | 2–2 | Stourport Swifts |
| 23 | Bemerton Heath Harlequins | 0–1 | Brislington |
| 24 | Berkhamsted Town | 2–2 | Bishop's Stortford |
| 25 | Billingham Town | 1–2 | Fleetwood Freeport |
| 26 | Bilston Town | 2–4 | Oadby Town |
| 27 | Blackstone | 0–0 | Willenhall Town |
| 28 | Bognor Regis Town | 2–1 | Didcot Town |
| 29 | Bootle | 0–0 | Jarrow Roofing Boldon Community Association |
| 30 | Borrowash Victoria | 0–1 | Sutton Coldfield Town |
| 31 | Boston Town | 1–0 | Boldmere St Michaels |
| 32 | Bourne Town | 0–2 | Stewarts & Lloyds Corby |
| 33 | Bowers United | 4–0 | Hanwell Town |
| 34 | Brackley Town | 2–1 | Long Buckby |
| 35 | Bracknell Town | 2–2 | Camberley Town |
| 36 | Bradford Park Avenue | 1–0 | Prescot Cables |
| 37 | Braintree Town | 1–1 | Leyton Pennant |
| 38 | Brandon United | 0–3 | Ossett Town |
| 39 | Bridgnorth Town | 1–3 | Hinckley United |
| 40 | Bridgwater Town | 0–5 | Lymington & New Milton |
| 41 | Brodsworth Miners Welfare | 1–0 | South Shields |
| 42 | Burnham | 0–1 | Wisbech Town |
| 43 | Burnham Ramblers | 1–2 | Hoddesdon Town |
| 44 | Chalfont St Peter | 0–6 | Barking |
| 45 | Cheadle Town | 0–3 | Warrington Town |
| 46 | Chester-Le-Street Town | 1–3 | St Helens Town |
| 47 | Chichester City | 2–2 | Selsey |
| 48 | Chippenham Town | 1–0 | Bournemouth |
| 49 | Chipstead | 0–5 | Tonbridge Angels |
| 50 | Christchurch | 1–1 | Bridport |
| 51 | Cirencester Town | 3–0 | B A T Sports |
| 52 | Cobham | 1–1 | Farnham Town |
| 53 | Concord Rangers | 2–2 | East Thurrock United |
| 54 | Cray Wanderers | 2–2 | Portfield |
| 55 | Crook Town | 2–0 | Yorkshire Amateur |
| 56 | Curzon Ashton | 0–1 | Brigg Town |
| 57 | Darwen | 0–1 | Billingham Synthonia |
| 58 | Deal Town | 5–0 | Greenwich Borough |
| 59 | Denaby United | 0–2 | Chorley |
| 60 | Desborough Town | 2–3 | Northampton Spencer |
| 61 | Diss Town | 1–6 | A F C Sudbury |
| 62 | Downton | 3–6 | Barnstaple Town |
| 63 | Dunston Federation Brewery | 1–0 | Maine Road |
| 64 | Easington Colliery | 2–2 | Newcastle Blue Star |
| 65 | East Cowes Victoria Athletic | 0–1 | Sittingbourne |
| 66 | Eastbourne Town | 0–0 | Three Bridges |
| 67 | Egham Town | 0–2 | Croydon |
| 68 | Ely City | 2–3 | Witham Town |
| 69 | Epsom & Ewell | 0–3 | Worthing |
| 70 | Erith & Belvedere | 0–2 | Wick |
| 71 | Erith Town | 0–0 | Dorking |
| 72 | Fakenham Town | 3–2 | Brook House |
| 73 | Falmouth Town | 1–2 | Bideford |
| 74 | Fareham Town | 0–1 | Carterton Town |
| 75 | Farsley Celtic | 1–1 | Guisborough Town |
| 76 | Felixstowe Port & Town | 1–3 | Wingate & Finchley |
| 77 | Fleet Town | 1–3 | Lewes |
| 78 | Flixton | 2–1 | Northallerton Town |
| 79 | Folkestone Invicta | 4–2 | Croydon Athletic |
| 80 | Ford Sports Daventry | 1–2 | Nantwich Town |
| 81 | Ford United | 5–1 | Edgware Town |
| 82 | Frome Town | 0–4 | Cinderford Town |
| 83 | Garforth Town | 0–4 | Armthorpe Welfare |
| 84 | Glapwell | 3–1 | Stapenhill |
| 85 | Glasshoughton Welfare | 0–1 | Hebburn |
| 86 | Godalming & Guildford | 1–2 | Horsham Y M C A |
| 87 | Goole | 1–1 | Trafford |
| 88 | Gorleston | 1–1 | Lowestoft Town |
| 89 | Grays Athletic | 7–1 | Basildon United |
| 90 | Great Wakering Rovers | 0–0 | Staines Town |
| 91 | Great Yarmouth Town | 5–3 | Tilbury |
| 92 | Gresley Rovers | 0–1 | Eastwood Town |
| 93 | Gretna | 5–0 | Rossington Main |
| 94 | Hailsham Town | 5–1 | Littlehampton Town |
| 95 | Halesowen Harriers | 4–0 | West Midlands Police |
| 96 | Hallam | 1–2 | Liversedge |
| 97 | Halstead Town | 1–3 | Royston Town |
| 98 | Harrogate Railway Athletic | 1–0 | Willington |
| 99 | Harwich & Parkeston | 2–3 | Harlow Town |
| 100 | Hastings Town | 6–1 | Southwick |
| 101 | Hemel Hempstead Town | 4–0 | Harpenden Town |
| 102 | Herne Bay | 1–0 | Canterbury City |
| 103 | Hertford Town w/o-scr Barkingside | ||
| 104 | Hillingdon Borough | 1–1 | St Leonards |
| 105 | Histon | 1–0 | Hullbridge Sports |
| 106 | Holbeach United | 2–0 | Pelsall Villa |
| 107 | Horsham | 0–1 | Hassocks |
| 108 | Hythe United | 0–0 | Burgess Hill Town |
| 109 | Kingsbury Town | 2–1 | Tring Town |
| 110 | Knypersley Victoria | 0–2 | Bedworth United |
| 111 | Leatherhead | 0–1 | Cowes Sports |
| 112 | Lincoln United | 1–2 | Mickleover Sports |
| 113 | Louth United | 2–1 | Kennek Ryhope Community Association |
| 114 | Mangotsfield United | 3–0 | Hungerford Town |
| 115 | Marlow | 2–2 | Barton Rovers |
| 116 | Marske United | 1–1 | Ashington |
| 117 | Matlock Town | 1–0 | Chasetown |
| 118 | Melksham Town | 1–3 | Evesham United |
| 119 | Merstham | 1–5 | Corinthian Casuals |
| 120 | Metropolitan Police | 2–1 | Chertsey Town |
| 121 | Minehead Town | 1–3 | Elmore |
| 122 | Molesey | 3–1 | Ringmer |
| 123 | Moor Green | 3–0 | Paget Rangers |
| 124 | Morpeth Town | 2–1 | Harrogate Town |
| 125 | Mossley | 2–1 | Atherton Laburnum Rovers |
| 126 | Netherfield Kendal | 3–0 | Oldham Town |
| 127 | Newcastle Town | 1–0 | Sandwell Borough |
| 128 | Newport I O W | 2–0 | North Leigh |
| 129 | North Ferriby United | 1–0 | Witton Albion |
| 130 | Northwood | 8–0 | Clapton |
| 131 | Oxford City | 5–1 | Gosport Borough |
| 132 | Parkgate | 1–5 | Eccleshill United |
| 133 | Paulton Rovers | 1–2 | Odd Down |
| 134 | Penrith | 4–0 | Shotton Comrades |
| 135 | Pickering Town | 4–1 | Horden Colliery Welfare |
| 136 | Potters Bar Town | 3–3 | Flackwell Heath |
| 137 | Racing Club Warwick | 1–2 | Blakenall |
| 138 | Radcliffe Borough | 2–1 | Durham City |
| 139 | Ramsgate | 2–1 | Dartford |
| 140 | Raynes Park Vale | 1–2 | Fisher Athletic London |
| 141 | Redditch United | 1–0 | Kings Norton Town |
| 142 | Redhill | 2–0 | Slade Green |
| 143 | Rocester | 2–3 | Spalding United |
| 144 | Romford | 1–0 | Maldon Town |
| 145 | Rossendale United | 2–0 | Chadderton |
| 146 | Ruislip Manor | 2–0 | Leighton Town |
| 147 | Saffron Walden Town | 5–0 | Kempston Rovers |
| 148 | Salford City | 2–0 | Evenwood Town |
| 149 | Saltdean United | 1–0 | Beckenham Town |
| 150 | Sandhurst Town | 0–0 | A F C Newbury |
| 151 | Seaham Red Star | 2–1 | West Auckland Town |
| 152 | Selby Town | 0–3 | Bedlington Terriers |
| 153 | Shepshed Dynamo | 0–3 | Raunds Town |
| 154 | Shifnal Town | 3–3 | Rushall Olympic |
| 155 | Shildon | 1–3 | Thornaby-On-Tees |
| 156 | Shoreham | 1–2 | Abingdon United |
| 157 | Skelmersdale United | 5–2 | Whitley Bay |
| 158 | Soham Town Rangers | 7–0 | Buckingham Town |
| 159 | Southall | 2–5 | Witney Town |
| 160 | Southend Manor | 4–0 | Ilford |
| 161 | St Blazey | 3–1 | Brockenhurst |
| 162 | St Neots Town | 2–1 | Hornchurch |
| 163 | Stafford Rangers | 2–0 | Glossop North End |
| 164 | Stamford | 3–1 | Corby Town |
| 165 | Stotfold | 0–0 | Wembley |
| 166 | Stourbridge | 3–1 | Bromsgrove Rovers |
| 167 | Stowmarket Town | 3–0 | Welwyn Garden City |
| 168 | Stratford Town | 4–1 | Leek C S O B |
| 169 | Street | 0–1 | Eastleigh |
| 170 | Thackley | 0–1 | Consett |
| 171 | Thamesmead Town | 2–2 | Reading Town |
| 172 | Thatcham Town | 4–2 | Lordswood |
| 173 | Tiptree United | 2–0 | London Colney |
| 174 | Tiverton Town | 7–1 | Pershore Town |
| 175 | Tow Law Town | 6–0 | Tadcaster Albion |
| 176 | Uxbridge | 0–1 | Wroxham |
| 177 | V S Rugby | 1–2 | Solihull Borough |
| 178 | Viking Greenford | 3–2 | Whitstable Town |
| 179 | Waltham Abbey | 1–1 | Yeading |
| 180 | Warboys Town | 3–3 | Bury Town |
| 181 | Ware | 3–0 | Newmarket Town |
| 182 | Watton United | 0–1 | Arlesey Town |
| 183 | Wealdstone | 1–0 | Clacton Town |
| 184 | Wednesfield | 1–6 | Oldbury United |
| 185 | Wellingborough Town | 3–0 | Kidsgrove Athletic |
| 186 | Welton Rovers | 4–0 | Warminster Town |
| 187 | Westbury United | 0–1 | Devizes Town |
| 188 | Whitehawk | 0–1 | Maidenhead United |
| 189 | Whyteleafe | 4–3 | Lancing |
| 190 | Windsor & Eton | 0–0 | Bromley |
| 191 | Wivenhoe Town | 0–1 | Bedford Town |
| 192 | Wokingham Town | 1–4 | Sheppey United |
| 193 | Woodbridge Town | 1–5 | Chelmsford City |
| 194 | Woodley Sports | 2–1 | Ossett Albion |
| 195 | Wootton Blue Cross | 0–2 | Cheshunt |
| 196 | Workington | 1–2 | Burscough |
| 197 | Yate Town | 0–3 | Taunton Town |
Replays
| Tie | Home Team | Score | Away Team | |
|---|---|---|---|---|
| 5 | Yaxley | 1–2 | Arnold Town | |
| 14 | Sheffield | 4–0 | Bacup Borough | |
| 18 | Staveley Miners Welfare | 5–3 | Barwell | |
| 22 | Stourport Swifts | 1–2 | Belper Town | |
| 24 | Bishop's Stortford | 3–3 | Berkhamsted Town | |
| (Bishop's Stortford won 4–2 on penalties) | ||||
| 27 | Willenhall Town | 4–2 | Blackstone | |
| 29 | Jarrow Roofing Boldon Community Association | 1–1 | Bootle | |
| (Jarrow Roofing won 5–4 on penalties) | ||||
| 35 | Camberley Town | 1–3 | Bracknell Town | |
| 37 | Leyton Pennant | 1–2 | Braintree Town | |
| 47 | Selsey | 4–2 | Chichester City | |
| 50 | Bridport | 2–4 | Christchurch | |
| 52 | Farnham Town | 3–2 | Cobham | |
| 53 | East Thurrock United | 4–2 | Concord Rangers | |
| 54 | Portfield | 2–3 | Cray Wanderers | |
| 64 | Newcastle Blue Star | 4–0 | Easington Colliery | |
| 66 | Three Bridges | 1–1 | Eastbourne Town | |
| (Eastbourne Town won 4–3 on penalties) | ||||
| 71 | Dorking | 1–2 | Erith Town | |
| 75 | Guisborough Town | 0–1 | Farsley Celtic | |
| 87 | Trafford | 6–3 | Goole | |
| 88 | Lowestoft Town | 1–2 | Gorleston | |
| 90 | Staines Town | 5–0 | Great Wakering Rovers | |
| 104 | St Leonards | 4–1 | Hillingdon Borough | |
| 108 | Burgess Hill Town | 3–0 | Hythe United | |
| 115 | Barton Rovers | 1–3 | Marlow | |
| 116 | Ashington | 1–2 | Marske United | |
| 136 | Flackwell Heath | 1–0 | Potters Bar Town | |
| 150 | A F C Newbury | 5–2 | Sandhurst Town | |
| 154 | Rushall Olympic | 0–1 | Shifnal Town | |
| 165 | Wembley | 2–1 | Stotfold | |
| 171 | Reading Town | 1–0 | Thamesmead Town | |
| 179 | Yeading | 1–3 | Waltham Abbey | |
| 180 | Bury Town | 2–2 | Warboys Town | |
| (Warboys Town won 4–3 on penalties) | ||||
| 190 | Bromley | 3–0 | Windsor & Eton | |
1st qualifying round
Ties
| Tie | Home Team | Score | Away Team |
|---|---|---|---|
| 1 | A F C Newbury | 3–1 | Portsmouth Royal Navy |
| 2 | A F C Sudbury | 1–0 | Flackwell Heath |
| 3 | Abingdon United | 0–6 | Oxford City |
| 4 | Arlesey Town | 4–1 | Bowers United |
| 5 | Ashford Town (Kent) | 0–2 | Fisher Athletic London |
| 6 | Ashton United | 2–0 | Flixton |
| 7 | Backwell United | 5–0 | Bashley |
| 8 | Banbury United | 6–3 | Gorleston |
| 9 | Barking | 0–1 | Grays Athletic |
| 10 | Bedfont | 5–1 | Reading Town |
| 11 | Bedford Town | 0–0 | Aveley |
| 12 | Bedlington Terriers | 2–0 | Stocksbridge Park Steels |
| 13 | Bedworth United | 1–3 | Redditch United |
| 14 | Bishop's Stortford | 4–2 | Hemel Hempstead Town |
| 15 | Bracknell Town | 2–4 | Tooting & Mitcham United |
| 16 | Bradford Park Avenue | 2–1 | Skelmersdale United |
| 17 | Brigg Town | 4–0 | Harrogate Railway Athletic |
| 18 | Carterton Town | 1–4 | Herne Bay |
| 19 | Chatham Town | 2–3 | Newport I O W |
| 20 | Cheshunt | 1–0 | Waltham Abbey |
| 21 | Chippenham Town | 2–1 | St Blazey |
| 22 | Chorley | 3–0 | Seaham Red Star |
| 23 | Christchurch | 1–0 | Brislington |
| 24 | Cinderford Town | 0–1 | Barnstaple Town |
| 25 | Cirencester Town | 2–2 | Taunton Town |
| 26 | Consett | 0–2 | Accrington Stanley |
| 27 | Corinthian Casuals | 4–0 | Sheppey United |
| 28 | Crook Town | 5–0 | Armthorpe Welfare |
| 29 | Croydon | 1–3 | Whyteleafe |
| 30 | Deal Town | 2–0 | Metropolitan Police |
| 31 | Devizes Town | 0–2 | Weston Super Mare |
| 32 | Dunston Federation Brewery | 1–0 | Salford City |
| 33 | East Thurrock United | 1–2 | Baldock Town |
| 34 | Eastbourne Town | 0–4 | Langney Sports |
| 35 | Eastwood Town | 3–0 | Holbeach United |
| 36 | Eccleshill United | 4–0 | Marske United |
| 37 | Elmore | 0–3 | Welton Rovers |
| 38 | Fakenham Town | 1–3 | Staines Town |
| 39 | Farnham Town | 3–0 | Selsey |
| 40 | Farsley Celtic | 1–1 | Burscough |
| 41 | Folkestone Invicta | 1–3 | Ramsgate |
| 42 | Great Yarmouth Town | 2–3 | Warboys Town |
| 43 | Hailsham Town | 1–3 | Sittingbourne |
| 44 | Halesowen Harriers | 1–4 | Arnold Town |
| 45 | Hassocks | 1–1 | Bromley |
| 46 | Hebburn | 2–2 | Louth United |
| 47 | Hertford Town | 0–2 | Royston Town |
| 48 | Hinckley United | 1–0 | Glapwell |
| 49 | Horsham Y M C A | 3–0 | Cray Wanderers |
| 50 | Kingsbury Town | 0–1 | Chelmsford City |
| 51 | Lewes | 3–3 | Erith Town |
| 52 | Liversedge | 3–2 | Woodley Sports |
| 53 | Lymington & New Milton | 3–0 | Bideford |
| 54 | Maidenhead United | 5–0 | Viking Greenford |
| 55 | Mangotsfield United | 1–1 | Odd Down |
| 56 | Marlow | 7–0 | Histon |
| 57 | Molesey | 0–3 | Hastings Town |
| 58 | Moor Green | 3–2 | Mickleover Sports |
| 59 | Mossley | 0–2 | Gretna |
| 60 | Nantwich Town | 3–0 | Stewarts & Lloyds Corby |
| 61 | Newcastle Blue Star | 1–1 | Billingham Synthonia |
| 62 | North Ferriby United | 3–2 | Netherfield Kendal |
| 63 | Northampton Spencer | 1–1 | Boston Town |
| 64 | Northwood | 2–0 | Stowmarket Town |
| 65 | Oldbury United | 2–0 | Stratford Town |
| 66 | Penrith | 0–2 | Morpeth Town |
| 67 | Radcliffe Borough | 8–1 | Warrington Town |
| 68 | Ramsbottom United | 1–2 | Fleetwood Freeport |
| 69 | Redhill | 1–1 | Burgess Hill Town |
| 70 | Romford | 4–1 | Southend Manor |
| 71 | Rossendale United | 1–1 | Ossett Town |
| 72 | Ruislip Manor | 0–1 | Beaconsfield S Y C O B |
| 73 | Saffron Walden Town | 3–2 | Hoddesdon Town |
| 74 | Sheffield | 1–0 | Brodsworth Miners Welfare |
| 75 | Shifnal Town | 2–3 | Congleton Town |
| 76 | Solihull Borough | 1–0 | Sutton Coldfield Town |
| 77 | Spalding United | 1–0 | Raunds Town |
| 78 | St Helens Town | 1–1 | Pickering Town |
| 79 | St Leonards | 0–1 | Bognor Regis Town |
| 80 | St Neots Town | 0–4 | Witham Town |
| 81 | Stafford Rangers | 2–2 | Matlock Town |
| 82 | Stamford | 3–1 | Brackley Town |
| 83 | Staveley Miners Welfare | 1–3 | Blakenall |
| 84 | Stourbridge | 0–2 | Belper Town |
| 85 | Thame United | 3–1 | Wick |
| 86 | Thatcham Town | 4–0 | Cowes Sports |
| 87 | Thornaby-On-Tees | 1–5 | Tow Law Town |
| 88 | Tiptree United | 1–2 | Witney Town |
| 89 | Tiverton Town | 4–3 | Evesham United |
| 90 | Tonbridge Angels | 3–0 | Abingdon Town |
| 91 | Torrington | 0–2 | Wimborne Town |
| 92 | Trafford | 3–3 | Jarrow Roofing Boldon Community Association |
| 93 | Tuffley Rovers | 2–1 | Eastleigh |
| 94 | Ware | 1–1 | Soham Town Rangers |
| 95 | Wealdstone | 1–1 | Ford United |
| 96 | Wellingborough Town | 2–2 | Newcastle Town |
| 97 | Wembley | 3–1 | Harlow Town |
| 98 | Willenhall Town | 1–1 | Oadby Town |
| 99 | Wingate & Finchley | 3–2 | Braintree Town |
| 100 | Wisbech Town | 3–1 | Wroxham |
| 101 | Worthing | 2–1 | Saltdean United |
Replays
| Tie | Home Team | Score | Away Team |
|---|---|---|---|
| 11 | Aveley | 1–2 | Bedford Town |
| 25 | Taunton Town | 4–0 | Cirencester Town |
| 40 | Burscough | 0–3 | Farsley Celtic |
| 45 | Bromley | 2–1 | Hassocks |
| 46 | Louth United | 4–2 | Hebburn |
| 51 | Erith Town | 3–4 | Lewes |
| 55 | Odd Down | 1–2 | Mangotsfield United |
| 61 | Billingham Synthonia | 3–2 | Newcastle Blue Star |
| 63 | Boston Town | 4–6 | Northampton Spencer |
| 69 | Burgess Hill Town | 3–0 | Redhill |
| 71 | Ossett Town | 2–0 | Rossendale United |
| 78 | Pickering Town | 3–2 | St Helens Town |
| 81 | Matlock Town | 0–4 | Stafford Rangers |
| 92 | Jarrow Roofing Boldon Community Association | 1–3 | Trafford |
| 94 | Soham Town Rangers | 2–1 | Ware |
| 95 | Ford United | 2–3 | Wealdstone |
| 96 | Newcastle Town | 0–4 | Wellingborough Town |
| 98 | Oadby Town | 3–1 | Willenhall Town |
2nd qualifying round
Ties
| Tie | Home Team | Score | Away Team | |
|---|---|---|---|---|
| 1 | A F C Sudbury | 1–2 | Dagenham & Redbridge | |
| 2 | Accrington Stanley | 0–2 | Whitby Town | |
| 3 | Aldershot Town | 6–1 | Lewes | |
| 4 | Ashton United | 0–2 | Brigg Town | |
| 5 | Aylesbury United | 1–3 | Chelmsford City | |
| 6 | Barnstaple Town | 2–3 | Backwell United | |
| 7 | Barrow | 2–2 | Marine | |
| 8 | Basingstoke Town | 0–0 | Merthyr Tydfil | |
| 9 | Bath City | 4–0 | Weston Super Mare | |
| 10 | Beaconsfield S Y C O B | 0–3 | King's Lynn | |
| 11 | Bedford Town | 0–2 | St Albans City | |
| 12 | Belper Town | 4–2 | Arnold Town | |
| 13 | Billingham Synthonia | 1–2 | North Ferriby United | |
| 14 | Bishop's Stortford | 1–1 | Wingate & Finchley | |
| 15 | Boston United | 3–1 | Oldbury United | |
| 16 | Bradford Park Avenue | 2–2 | Droylsden | |
| 17 | Bromley | 4–1 | Crawley Town | |
| 18 | Burgess Hill Town | 2–2 | Bedfont | |
| 19 | Cambridge City | 3–1 | Arlesey Town | |
| 20 | Canvey Island | 3–1 | Boreham Wood | |
| 21 | Carshalton Athletic | 2–2 | Sittingbourne | |
| 22 | Chesham United | 1–3 | Baldock Town | |
| 23 | Cheshunt | 0–0 | Witham Town | |
| 24 | Chippenham Town | 2–0 | Mangotsfield United | |
| 25 | Christchurch | 2–3 | Worcester City | |
| 26 | Clevedon Town | 2–1 | Tiverton Town | |
| 27 | Deal Town | 2–2 | Worthing | |
| 28 | Emley | 2–0 | Louth United | |
| 29 | Farnham Town | 2–2 | Herne Bay | |
| 30 | Frickley Athletic | 0–1 | Bedlington Terriers | |
| 31 | Gainsborough Trinity | 2–0 | Eccleshill United | |
| 32 | Gateshead | 3–0 | Winsford United | |
| 33 | Grantham Town | 6–0 | Northampton Spencer | |
| 34 | Gravesend & Northfleet | 1–1 | Fisher Athletic London | |
| 35 | Guiseley | 6–0 | Pickering Town | |
| 36 | Hampton & Richmond Borough | 1–1 | Bognor Regis Town | |
| 37 | Hastings Town | 3–1 | A F C Newbury | |
| 38 | Havant & Waterlooville | 2–2 | Langney Sports | |
| 39 | Hendon | 2–0 | Grays Athletic | |
| 40 | Heybridge Swifts | 1–2 | Romford | |
| 41 | Hinckley United | 2–0 | Wellingborough Town | |
| 42 | Horsham Y M C A | 4–0 | Corinthian Casuals | |
| 43 | Hyde United | 1–1 | Crook Town | |
| 44 | Lancaster City – Bye | |||
| (Fleetwood Freeport expelled for fielding ineligible player in Preliminary Round) | ||||
| 45 | Leek Town | 0–2 | Blakenall | |
| 46 | Leigh R M I | 5–3 | Blyth Spartans | |
| 47 | Liversedge | 1–2 | Dunston Federation Brewery | |
| 48 | Lymington & New Milton | 1–1 | Tuffley Rovers | |
| 49 | Marlow | 1–4 | Harrow Borough | |
| 50 | Moor Green | 2–1 | Atherstone United | |
| 51 | Morpeth Town | 2–1 | Tow Law Town | |
| 52 | Nantwich Town | 1–0 | Hucknall Town | |
| 53 | Newport County | 1–1 | Wimborne Town | |
| 54 | Newport I O W | 1–1 | Dulwich Hamlet | |
| 55 | Northwood | 3–3 | Rothwell Town | |
| 56 | Oadby Town | 2–1 | Halesowen Town | |
| 57 | Ossett Town | 2–1 | Spennymoor United | |
| 58 | Purfleet | 0–0 | Banbury United | |
| 59 | Radcliffe Borough | 0–1 | Chorley | |
| 60 | Ramsgate | 0–3 | Margate | |
| 61 | Redditch United | 0–1 | Burton Albion | |
| 62 | Royston Town | 1–3 | Wembley | |
| 63 | Runcorn | 2–0 | Gretna | |
| 64 | Saffron Walden Town | 1–4 | Hitchin Town | |
| 65 | Sheffield | 0–0 | Farsley Celtic | |
| 66 | Slough Town | 3–1 | Cowes Sports | |
| 67 | Soham Town Rangers | 1–3 | Enfield | |
| 68 | Solihull Borough | 3–4 | Ilkeston Town | |
| 69 | Stafford Rangers | 1–3 | Eastwood Town | |
| 70 | Staines Town | 0–3 | Wealdstone | |
| 71 | Stalybridge Celtic | 1–0 | Colwyn Bay | |
| 72 | Stamford | 1–1 | Congleton Town | |
| 73 | Tamworth | 6–1 | Spalding United | |
| 74 | Taunton Town | 3–0 | Dorchester Town | |
| 75 | Thame United | 0–1 | Whyteleafe | |
| 76 | Tonbridge Angels | 0–2 | Farnborough Town | |
| 77 | Tooting & Mitcham United | 0–2 | Oxford City | |
| 78 | Trafford | 2–2 | Bamber Bridge | |
| 79 | Walton & Hersham | 0–2 | Maidenhead United | |
| 80 | Warboys Town | 0–2 | Witney Town | |
| 81 | Welton Rovers | 1–3 | Salisbury City | |
| 82 | Weymouth | 0–0 | Gloucester City | |
| 83 | Wisbech Town | 1–3 | Billericay Town | |
| 84 | Worksop Town | 2–3 | Bishop Auckland | |
Replays
| Tie | Home Team | Score | Away Team | |
|---|---|---|---|---|
| 7 | Marine | 3–2 | Barrow | |
| 8 | Merthyr Tydfil | 2–1 | Basingstoke Town | |
| 14 | Wingate & Finchley | 3–2 | Bishop's Stortford | |
| 16 | Droylsden | 2–1 | Bradford Park Avenue | |
| 18 | Bedfont | 0–2 | Burgess Hill Town | |
| 21 | Sittingbourne | 0–1 | Carshalton Athletic | |
| 23 | Witham Town | 0–2 | Cheshunt | |
| 27 | Worthing | 3–0 | Deal Town | |
| 29 | Herne Bay | 1–1 | Farnham Town | |
| (Herne Bay won 4–3 on penalties, later declared void) | ||||
| 34 | Fisher Athletic London | 2–1 | Gravesend & Northfleet | |
| 36 | Bognor Regis Town | 0–0 | Hampton & Richmond Borough | |
| (Bognor Regis won 5–4 on penalties) | ||||
| 38 | Langney Sports | 2–1 | Havant & Waterlooville | |
| 43 | Crook Town | 2–1 | Hyde United | |
| 48 | Tuffley Rovers | 0–5 | Lymington & New Milton | |
| 53 | Wimborne Town | 0–3 | Newport County | |
| 54 | Dulwich Hamlet | 4–1 | Newport I O W | |
| 55 | Rothwell Town | 2–0 | Northwood | |
| 58 | Banbury United | 0–1 | Purfleet | |
| 65 | Farsley Celtic | 2–1 | Sheffield | |
| 72 | Congleton Town | 2–0 | Stamford | |
| 78 | Bamber Bridge | 2–1 | Trafford | |
| 82 | Gloucester City | 2–1 | Weymouth | |
2nd replay
| Tie | Home Team | Score | Away Team |
|---|---|---|---|
| 29 | Farnham Town | 1–2 | Herne Bay |
3rd qualifying round
Ties
| Tie | Home Team | Score | Away Team |
|---|---|---|---|
| 1 | Backwell United | 2–4 | Oxford City |
| 2 | Baldock Town | 5–1 | Cheshunt |
| 3 | Bamber Bridge | 3–0 | Morpeth Town |
| 4 | Bath City | 3–1 | Farnborough Town |
| 5 | Belper Town | 1–2 | Tamworth |
| 6 | Bishop Auckland | 1–1 | Bedlington Terriers |
| 7 | Bognor Regis Town | 1–0 | Bromley |
| 8 | Boston United | 4–0 | Purfleet |
| 9 | Cambridge City | 1–0 | King's Lynn |
| 10 | Chelmsford City | 1–0 | Moor Green |
| 11 | Chippenham Town | 1–1 | Worthing |
| 12 | Dagenham & Redbridge | 0–2 | Burton Albion |
| 13 | Droylsden | 2–2 | Gainsborough Trinity |
| 14 | Dulwich Hamlet | 2–1 | Hastings Town |
| 15 | Dunston Federation Brewery | 0–2 | Runcorn |
| 16 | Eastwood Town | 3–0 | Oadby Town |
| 17 | Enfield | 2–0 | Billericay Town |
| 18 | Fisher Athletic London | 1–2 | Aldershot Town |
| 19 | Gateshead | 4–0 | Brigg Town |
| 20 | Gloucester City | 2–3 | Merthyr Tydfil |
| 21 | Hendon | 2–1 | Blakenall |
| 22 | Herne Bay | 0–3 | Horsham Y M C A |
| 23 | Hitchin Town | 2–1 | Grantham Town |
| 24 | Lancaster City | 2–2 | Whitby Town |
| 25 | Leigh R M I | 1–1 | Crook Town |
| 26 | Lymington & New Milton | 3–1 | Clevedon Town |
| 27 | Maidenhead United | 0–1 | Salisbury City |
| 28 | Marine | 2–0 | Chorley |
| 29 | Newport County | 1–2 | Burgess Hill Town |
| 30 | North Ferriby United | 1–3 | Guiseley |
| 31 | Ossett Town | 0–0 | Emley |
| 32 | Romford | 6–0 | Congleton Town |
| 33 | Slough Town | 1–0 | Sittingbourne |
| 34 | St Albans City | 4–2 | Nantwich Town |
| 35 | Stalybridge Celtic | 4–2 | Farsley Celtic |
| 36 | Taunton Town | 0–3 | Margate |
| 37 | Wealdstone | 1–1 | Rothwell Town |
| 38 | Wembley | 0–3 | Canvey Island |
| 39 | Whyteleafe | 1–0 | Langney Sports |
| 40 | Wingate & Finchley | 0–5 | Ilkeston Town |
| 41 | Witney Town | 2–1 | Hinckley United |
| 42 | Worcester City | 3–2 | Harrow Borough |
Replays
| Tie | Home Team | Score | Away Team | |
|---|---|---|---|---|
| 6 | Bedlington Terriers | 0–1 | Bishop Auckland | |
| 11 | Worthing | 3–1 | Chippenham Town | |
| 13 | Gainsborough Trinity | 1–2 | Droylsden | |
| 24 | Whitby Town | 2–2 | Lancaster City | |
| (Lancaster City won 4–2 on penalties) | ||||
| 25 | Crook Town | 2–1 | Leigh R M I | |
| 31 | Emley | 4–1 | Ossett Town | |
| 37 | Rothwell Town | 2–0 | Wealdstone | |
4th qualifying round
Ties
| Tie | Home Team | Score | Away Team |
|---|---|---|---|
| 1 | Altrincham | 0–0 | Stalybridge Celtic |
| 2 | Bognor Regis Town | 0–1 | Whyteleafe |
| 3 | Canvey Island | 3–3 | St Albans City |
| 4 | Doncaster Rovers | 7–0 | Crook Town |
| 5 | Droylsden | 0–2 | Eastwood Town |
| 6 | Dulwich Hamlet | 0–0 | Hayes |
| 7 | Enfield | 1–1 | Baldock Town |
| 8 | Hendon | 1–0 | Margate |
| 9 | Hereford United | 4–1 | Burgess Hill Town |
| 10 | Horsham Y M C A | 2–3 | Chelmsford City |
| 11 | Ilkeston Town | 3–0 | Romford |
| 12 | Kingstonian | 0–0 | Boston United |
| 13 | Lancaster City | 0–0 | Bamber Bridge |
| 14 | Lymington & New Milton | 1–3 | Aldershot Town |
| 15 | Marine | 1–1 | Runcorn |
| 16 | Merthyr Tydfil | 2–0 | Hitchin Town |
| 17 | Morecambe | 1–0 | Bishop Auckland |
| 18 | Northwich Victoria | 2–2 | Hednesford Town |
| 19 | Nuneaton Borough | 2–3 | Guiseley |
| 20 | Oxford City | 2–1 | Salisbury City |
| 21 | Rothwell Town | 1–1 | Kettering Town |
| 22 | Rushden & Diamonds | 4–1 | Sutton United |
| 23 | Scarborough | 0–1 | Tamworth |
| 24 | Slough Town | 1–1 | Cambridge City |
| 25 | Southport | 1–1 | Emley |
| 26 | Stevenage Borough | 1–1 | Bath City |
| 27 | Telford United | 0–0 | Gateshead |
| 28 | Welling United | 2–0 | Kidderminster Harriers |
| 29 | Woking | 1–1 | Burton Albion |
| 30 | Worcester City | 2–5 | Forest Green Rovers |
| 31 | Worthing | 1–1 | Dover Athletic |
| 32 | Yeovil Town | 2–1 | Witney Town |
Replays
| Tie | Home Team | Score | Away Team | |
|---|---|---|---|---|
| 1 | Stalybridge Celtic | 3–2 | Altrincham | |
| 1 | Stalybridge Celtic | 2–1 | Altrincham | |
| (Ordered to be replayed) | ||||
| 3 | St Albans City | 2–1 | Canvey Island | |
| 6 | Hayes | 3–0 | Dulwich Hamlet | |
| 7 | Baldock Town | 2–2 | Enfield | |
| (Enfield won 4–2 on penalties) | ||||
| 12 | Boston United | 0–3 | Kingstonian | |
| 13 | Bamber Bridge | 4–3 | Lancaster City | |
| 15 | Runcorn | 3–2 | Marine | |
| 18 | Hednesford Town | 1–0 | Northwich Victoria | |
| 21 | Kettering Town | 2–1 | Rothwell Town | |
| 24 | Cambridge City | 3–2 | Slough Town | |
| 25 | Emley | 0–2 | Southport | |
| 26 | Bath City | 1–0 | Stevenage Borough | |
| 27 | Gateshead | 2–1 | Telford United | |
| 29 | Burton Albion | 3–1 | Woking | |
| 31 | Dover Athletic | 0–1 | Worthing | |
1999–2000 FA Cup
See 1999-2000 FA Cup for details of the rounds from the First Round Proper onwards.
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