Tripp won the 1975 and 1976 USAC National Midget Championship. He stayed on the national tour for more several years before he started racing on the Western States series. He consistently placed in the first or second place in the series' points, winning championships in 1983, 1985, 1987, 1988, 1990, 1991 and 1992. He reached his 100th win in 1998. Sleepy sits on top of the Western States Feature list with 104 wins.
He also had 59 National Midget car victories, which places him fifth on USAC's all-time National Midget Car Series Feature Winners list, placing him 11th on USAC's all-time National Career Feature Victories. His combined National, Western and Regional USAC wins have him with over 250 careers wins to his name.
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