Diamond Resorts Invitational

In 2013, PGA Tour professional, Brian Gay, offered to lend his name to the inaugural Diamond Resorts-sponsored golf invitational in an effort to help raise money for Florida Hospital for Children. More than 300 golfers, celebrities and spectators attended the event. The tournament also hosted a celebrity-only golf tournament with a $40,000 purse. PGA Tour professional Nick O'Hern won the Professional Golf Division and retired NFL player Mark Rypien was the celebrity champion.[8]

In its second year, the Diamond Resorts Invitational was held at Isleworth Country Club in Windermere, Florida from December 11–14, 2014. More than 400 people participated in the weekend event, which included a celebrity/amateur golf tournament and private concert by country music artist Colt Ford.[9] PGA Tour professional J. B. Holmes won the PGA Tour Division, shooting a 9-under 63. The celebrity champion was former Atlanta Braves pitcher John Smoltz, who defeated the President of Baseball Operations for the Atlanta Brave, John Hart, in a one-hole playoff, for the first of his three victories in the event (including the successor tournament).

In 2016, the golf event was named Diamond Resorts Invitational benefiting Florida Hospital for Children and was nationally televised on the Golf Channel with an 81-person field, 54-hole celebrity tournament. It was held January 12–17, 2016 at The Golden Bear Club in Windermere, Florida and featured a Stableford scoring format with a $500,000 purse. After three days of play, former professional American tennis player, Mardy Fish, claimed victory.[10] The celebrity lineup included Super Bowl MVPs Jerry Rice, Marcus Allen, Richard Dent and Mark Rypien; Atlanta Braves Hall of Fame pitcher of Greg Maddux, John Smoltz and Tom Glavine; ESPN college football expert and former NFL quarterback Danny Kanell; baseball legends Reggie Jackson, Roger Clemens and Gaylord Perry; and celebrity entertainers Larry The Cable Guy, Jake Owen and Colt Ford.

In 2017, the tournament became a PGA Tour Champions Challenge Season event. It was held Jan. 13-15 at Tranquilo Golf Club at Four Seasons Resort Orlando. It had 27 PGA Tour Champions players, three LPGA players and 48 other amateur celebrity players. The players were organized into threesomes of one professional and two celebrities, and competed side-by-side in a Modified Stableford scoring format for separate purses totaling $1.25 million. PGA Champions Tour player Woody Austin won the professional division[11] and MLB pitcher Mark Mulder won the celebrity division.[12]

The tournament was a PGA Tour Champions Challenge Season event again in 2018 and held Jan. 12-14 at Tranquilo Golf Club at Four Seasons Resort Orlando. The professional field featured 28 PGA Tour Champions players and four LPGA players, including Brittany Lincicome and Brooke Henderson, competing for a $750,000 purse. The celebrity field featured 50 sports and entertainment players competing for their own $500,000 purse. All three days of the tournament were again nationally televised on Golf Channel. Former top-ranked American tennis player Mardy Fish took home the $100,000 first place prize money in the celebrity division, while PGA TOUR Champions standout Scott Parel pocketed $125,000 by winning the professional division after a first hole playoff, his second victory in the event. (National Baseball Hall of Fame pitcher John Smoltz would surpass him with consecutive wins in 2019 and 2020, as the celebrity tournament lineage is now part of the LPGA Tournament of Champions.)[13]