Adelaide 500

The 1999 event saw Craig Lowndes win the Saturday race, only to be disqualified due to his involvement in an accident with Danny Osborne, and made to start from the back of the grid for race two on the Sunday. Lowndes passed every car in the field to also win race two and thus become the first winner of the Adelaide 500, in what remains his only event victory. Lowndes' disqualification from race one was later overturned.[12] The 1999 race was also controversial as the original regulations stated the race was one 500 kilometre race with an overnight break at the 250 km mark. When a significant portion of high-profile cars retired in the first leg, the regulations were changed overnight to allow those cars to start the Sunday race.[13][14] The inaugural event also proved a challenge to the fitness of the drivers, with both Paul Radisich and John Faulkner requiring medical assistance due to dehydration.[15]

Pit straight during qualifying on Friday 2008.

The 2000 event once again saw a last-to-first drive, with Mark Skaife winning the Sunday race after starting 38th due to a DNF on Saturday.[12] Despite this, the event win was awarded to Garth Tander, the only occasion in which the Sunday winner was not awarded the event win.[16] In 2001 Clipsal 500, Craig Lowndes won his first race for Ford since his defection from the Holden Racing Team to a Gibson Motorsport Ford. After winning the Saturday race, he was again in contention on Sunday until an incident with his former teammate Skaife ended his charge.[12] In 2002, the track layout received its only modification to date, with Turn 8 being re-profiled to what became known as 'The Sweeper'. The change followed Brad Jones's roll-over at the previous version of the corner in 2000 among other incidents. The re-profiled corner became one of the most infamous corners in Australian motorsport with several high-profile victims in the first year including Radisich and Glenn Seton.[13] 2002 also saw a pre-qualifying session held, in the week leading into the event, at Mallala Motor Sport Park due to capacity and scheduling constraints at the Adelaide 500 event.[17]

Holden had dominated the event from 1999 to 2003, with three wins to Skaife and one each to Bright and Tander following Lowndes' inaugural event victory. It wasn't until 2004 that a Ford driver won the event, with Marcos Ambrose winning both races, repeating the feat in 2005. Ford's turn of fate was signified by a sweep of the top four in the Saturday race of the 2005 event.[12] Jamie Whincup then made it three in a row for Ford in 2006 with his first event win in Supercars in his first appearance for Triple Eight Race Engineering.[13] The 2007 event brought about the first instance of the driver who scored the most weekend points not winning the event. Brothers Todd Kelly and Rick Kelly won one race each across the weekend however Rick was credited with the event win for his Sunday race victory despite scoring less points in the other race.[13] Whincup went on to win again in 2008, 2009 and 2011 to be the most successful driver in the event's history to date. The 2008 event was, however, marred by the death of Ashley Cooper following a crash in the second-tier Fujitsu V8 Supercars Series race.

The Holden VF Commodore of Shane van Gisbergen at the 2013 Clipsal 500 Adelaide.

From 2002 to 2009, the Adelaide 500 was the opening round of the championship. It lost this position in 2010 and 2011, with the Yas V8 400 in the United Arab Emirates opening the series. From 2012, Adelaide returned to being the opening round.[18] The 2012 Clipsal 500 provided one of the event's most memorable finishes when Whincup chased down and overtook Will Davison on the final lap of the Saturday race. Whincup had made an additional pitstop and gained enough ground to take advantage when Davison's car began to run out of fuel. Davison went on to win the event with a win on Sunday, his first since joining Ford Performance Racing. The 2013 event was the first of the Car of the Future regulations, which saw Nissan and Mercedes-Benz join the series as the first manufacturers outside Ford and Holden since 1993. The Sunday race was won by Shane van Gisbergen in the aftermath of his controversial decision to announce his retirement during the 2012 season before switching teams to Tekno Autosports over the off-season.[15]

In 2014, Volvo rejoined the series and made an immediate impact with Scott McLaughlin fighting off Whincup on the final lap to finish second in the newly-introduced second 125 km race on Saturday.[15] On the Sunday, Jason Bright rolled his Brad Jones Racing car at the Senna Chicane, thirteen years after team boss Brad Jones rolled his car at Turn 8. James Courtney won the event and in 2015 became the fourth driver to win the Clipsal 500 back-to-back, after Skaife, Ambrose and Whincup. In doing so he also provided the Holden Racing Team with a record sixth and seventh event wins, two ahead of Triple Eight, who scored their fifth victory in 2017 with van Gisbergen. The intervening event in 2016 was disrupted by thunderstorms and heavy rain on the Sunday with Nick Percat eventually taking his first solo win and the only for Lucas Dumbrell Motorsport amidst a delayed start, confusion surrounding the fuel drop regulations and a red flag.[19]

Van Gisbergen swept the 2017 and 2018 editions of the event, taking four poles and four race victories in a return to the two by 250 km format.[20] The 2018 victory, in the twentieth running of the event, was the first victory for the Holden ZB Commodore in its debut appearance.[21] 2018 also saw the state of South Australia hosting two championship rounds for the first time since 1977 with The Bend Motorsport Park in Tailem Bend joining the calendar. In the return of the Ford Mustang nameplate to the championship in 2019, Scott McLaughlin achieved the same feat as van Gisbergen, winning the first championship race and round for the new car on debut. It was also the first race and round win for the Mustang nameplate since Allan Moffat at Oran Park in 1972, while McLaughlin's team's co-owner Dick Johnson had also won a non-championship race at the Adelaide Street Circuit in a Ford Mustang GT in 1985.[22]

In the week leading into the 2020 Adelaide 500, General Motors announced that the Holden brand, which was founded in Adelaide and has competed in every edition of the championship since its inception, would be retired by the end of the year.[23] The factory Holden team, run by Triple Eight Race Engineering, won the first race of the weekend with winner Jamie Whincup dedicating the win to Holden.[24] Whincup's team-mate van Gisbergen was leading the Sunday race until he was forced to make an additional pitstop for fuel due to a team error and then later suffered a mechanical failure and did not finish. This granted 2019 winner McLaughlin with a back to back event win.[25]

In October 2020, the event was cancelled, with the South Australian Tourism Commission announcing that the contract would be terminated one-year early and no renewal will be sought.[4] The COVID-19 pandemic, increased costs and falling interest due to no Falcons or Holdens racing [26] were cited by Premier of South Australia Steven Marshall as reasons for the event's demise.[27]

The Supercars category released a statement shortly after the announcement stating its 'regret' at the decision and willingness to return to Adelaide should the government 'decide to recommence...' the event in future.[28]

Previous event winners Mark Skaife[29] and Nick Percat[30] were among current and former drivers criticising the event's cancellation. South Australian Opposition Leader Peter Malinauskas launched a campaign via a South Australian Labor Party petition platform to restore the event,[31] and indicated an intent to return the Adelaide 500 should his party win government.[32]