Simpson was born in Bridgetown, Barbados; the son of Caymanian businessman David Simpson.[1] Simpson competes as Caymanian,[2] saying, "I really feel connected with the people of Cayman. It’s cool to fly the flag on the side of my car."[3]
Junior career
Formula 4 United States Championship
Simpson made his car racing debut in 2020 for Velocity Racing Development in the 2020 Formula 4 United States Championship after 9 years of karting across the Caribbean and United States.[4]
Formula Regional Americas Championship
Simpson would dovetail a season in the Formula 4 United States Championship with a season in the Formula Regional Americas Championship in 2020, and dominated the championship in his second season with podiums in all but five races.[5]
Winning the FR Americas title awarded Kyffin with a Honda Performance Development scholarship fund worth $600,000 towards a Super Formula campaign in 2022, but Japan’s ongoing travel restrictions due to COVID-19 prevented these plans coming to fruition.[6]
In 2022, Simpson signed a multi-year deal as a development driver with Chip Ganassi Racing, whilst also progressing to Indy Lights, partnering James Roe Jr. at TJ Speed Motorsports.[8] Following eight races with the team, Simpson moved to HMD Motorsports.[9] He finished ninth in the Indy Lights standings with a best result of fifth in Barber and Detroit.
Alongside his duties in junior formulae, Simpson would compete full-time in the 2023 Asian Le Mans Series together with James Allen and John Falb as part of Algarve Pro Racing[15] in preparation for a campaign in that year's European Le Mans Series.[16] The season opener in Dubai yielded a perfect start, as the trio took victory despite a spin from Falb.[17] Simpson played a major role in said victory, taking second place from Indy NXT rival Christian Bogle near half-distance, before closing the gap between himself and leader Ayhancan Güven from 25 to mere seven seconds by the end of their stints.[18] The following day, a puncture prevented the #25 from battling for a win; they eventually settled for fourth.[19] Race one at the Yas Marina Circuit saw Simpson battling the experienced Oliver Jarvis for a podium spot, however he would take himself out of contention owing to a spin into the turn 16 wall mere minutes before the end.[20][21] On Sunday, fourth place meant that Simpson, Allen and Falb would end up third in the LMP2 classification.[22]
European Le Mans Series
2023
Simpson would stay with Algarve Pro Racing to compete in the 2023 European Le Mans Series, where Simpson once again partnered James Allen, the pair being joined by Cadillac Hypercar driver Alex Lynn.[23] An unspectacular maiden race in Barcelona was followed by a markedly improved showing at the Circuit Paul Ricard, where Simpson's ability to stay close to leader Vladislav Lomko throughout the opening stints - exemplified by the Bajan setting the race's fastest lap - enabled teammates Lynn and Allen to get embroiled in the battle for victory, with the latter executing a late-race pass on Louis Delétraz to bring first place to APR.[24] Prior to the third race, held at MotorLand Aragón, Simpson received praise from Lynn, the Brit stating that "Kyffin is a fast learner" and praising him for his pace, whilst remarking that Simpson needed more experience.[25]
IndyCar
In January 2023, Kyffin completed his first NTT IndyCar Series test with Chip Ganassi Racing at Sebring International Raceway.[26] Following the end of the 2023 IndyCar season, Chip Ganassi announced that Simpson, who had been the team's development driver over the past two years, would be stepping up to IndyCar in 2024.[27][28] He started his season at St. Petersburg with a 12th place finish, ending up ahead of all other rookies and setting the fastest lap of the race.[29] Following three further top-20 finishes, Simpson ended up 21st in his first appearance at the Indy 500, having qualified a then-record 18th.[30][31]