In his 44 years behind the wheel, Cleary took down 14 track championships, including championships at the Norwood Arena, Seekonk, and Thompson. These championships have come behind the wheel of jalopies, cutdowns, full coupes, modifieds, pro-stocks, and mini modifieds. Driving a Florida modified in 1993 at age 63 Leo suffered 4 broken ribs and retired from racing although he can sometimes be found behind wheel of the #41 car at some NEAR events winning a feature at Seekonk Speedway in 2003.

Leo will be found at Waterford Speedbowl's Nostalgia Weekend on Saturday and Sunday July 31st and August 1st along with other members of the New England Auto Racers Hall of Fame including 1970 Daytona winner Pete Hamilton and 71 Indy 500 Rookie of the Year Denny Zimmerman.