A ten-time Motorsport champion member of the British Racing Drivers' Club, he competes in Europe, Australia & Asia in Le Mans LMP & GT cars.

In 2004, Winslow won the British ARP Formula 3 Championship in 2004, winning 10 races driving an older model car.

In September 2007, he took part in a Champ Car test at Sebring International Raceway with a view to securing a full-time drive in 2008,[1] but the series ultimately folded.

Winslow, driving for Team Meritus, won the Formula Asia V6 Championship at the last round of the season in Zhuhai, China, beating Armaan Ebrahim.

In 2009 Winslow drove in the American Atlantic Championship series for four different teams (primarily Genoa Racing) where his best result was 3rd and finished 6th after missing two events without a DNF.