Gregory only competed in four Grands Prix in the 1958 season, due to injuries sustained through one of his trademark bailouts when his car was set to crash, this time in a sports car race at Silverstone in England. He did manage a fourth place at the Italian Grand Prix, and a 6th in the last race of the year, this Moroccan Grand Prix. Moving to Cooper-Climax for the 1959 season alongside Jack Brabham and Bruce McLaren, he scored two podium finishes - a third place at the Dutch Grand Prix, and a career-best second at the Portuguese Grand Prix. However, he missed the final two races of the season, again due to injuries sustained jumping from a car moments before it crashed. He finished eighth in the Championship, and with teammate Brabham winning the World Championship, Cooper won their first Constructor's Championship. Gregory scored a pole position and set a course record at the non-Championship race at Aintree, but his contract with Cooper was not renewed for the following year.