He scored a significant win against Gunnar Nilsson and Rupert Keegan at the end of 1975 and then driving for Ron Dennis' Project Four team in Formula Two in 1976, 1977, and 1978, finishing runner-up to René Arnoux in the 1977 championship.

After failing to qualify for the first two races of the year in Argentina and Brazil in a Theodore, he made the grid in South Africa in a Hesketh, but retired early.

For the 1979 F2 championship, Cheever left Project Four and joined the Italian Osella team, taking three wins and fourth overall in their BMW-powered FA2.

However, the car was unreliable and Cheever managed just one finish all year, twelfth place at the team's home race in Italy.

He signed with the factory Equipe Renault team alongside Frenchman Alain Prost, both of whom were among the year's Championship favorites.

His best finish for Renault was second in the Canadian Grand Prix at the Circuit Gilles Villeneuve in Montreal, while earlier in the season he achieved his highest career qualifying position when he was second to teammate Prost at the French Grand Prix at the Paul Ricard Circuit.

However, when Michael was unable to obtain a FIA Superlicence for the race, Haas turned to the experienced Cheever, who quickly agreed to an F1 comeback.

He secured third place at the 1988 Italian Grand Prix at Monza; at one stage, he was almost disqualified when his Arrows A10B's 150-liter fuel tank was found to actually contain 151 liters.

Monza, won by the Ferrari of Gerhard Berger, was the only time the McLaren-Hondas of Alain Prost and 1988 World Champion Ayrton Senna did not win a race in 1988.

Cheever's third place in the 1988 Italian Grand Prix was also the final podium for the turbocharged I4 BMW M12 engine (badged as "Megatron" in 1987 and 1988).

His final podium finish came at the 1989 United States Grand Prix in his birthplace of Phoenix, where he was involved in a race-long battle with the Williams-Renault of former Alfa Romeo teammate Riccardo Patrese for second place, but then had to give way at the later stages of the race when his brakes started to fade (he claimed that one of his front brakes had actually stopped working).

During the last seconds of qualifying, he got out of shape coming out of the Fosters Hairpin onto the pit straight and clouted the wall hard with his Arrows A11-Ford, destroying the rear of the car.

Driving for A. J. Foyt's team, Cheever came closest to victory at Nazareth in 1995: he was leading the race on the last lap when he ran out of fuel.

In the Indy 500, Cheever was involved in a nasty lap 1 crash with Stan Fox, Carlos Guerrero and Lyn St. James.

Cheever ran for Team Menard for the three-race series, and at the 1996 Indianapolis 500, he set the fastest race lap to date at 236.103 mph (379.971 km/h).

In the championship's first-ever event at Kyalami International Raceway in South Africa, Cheever finished in eighth position.

Cheever finished fourth in the second GP Masters race on April 29, 2006, at the Losail International Circuit in Qatar.