In 1965, Leonard became teammates with Dan Gurney at Gurney's All American Racers team, driving the #29 All American Racers Hailbrand-Ford. During the season Leonard would get his first win when he won the Milwaukee 150 at Wisconsin State Fairgrounds Park Speedway. Leonard would also drive one race for legendary car builder and chief mechanic A. J. Watson at Leader Card Racing in the #2 Moog St. Louis Watson-Ford at the Langhorne 100 at Langhorne Speedway. At the end of the season Leonard finished 6th in the final point standings. In 1966, Leonard would continue to race for AAR on the paved ovals and road courses in the #6 Yamaha Eagle-Ford (although he did drive the #29 All American Bardahl Hailbrand-Ford at the Jimmy Bryan Memorial at Phoenix International Raceway) and would drive the #7 Vita Fresh Orange Juice Meskowski-Offenhauser at the dirt tracks (along with the Atlanta 300 at Atlanta Motor Speedway in the #11 Huffaker-Offenhauser. Leonard would get a best finish of 3rd place three times en route to a 4th-place finish in points. Also, during the season at the Indianapolis 500 Leonard would get his first top 10 in the historic race with a 9th-place finish.