He recorded extensively as both a leader and sideman. He came to public attention in the 1950s as a result of recording with Lee Konitz, André Previn, Stan Getz, Shorty Rogers, Chet Baker, Shelly Manne, Joe Castro and Serge Chaloff.
He played bass on Previn and Manne's My Fair Lady album, one of the most successful jazz records ever produced. He also performed on another of jazz's biggest hit albums, Eddie Harris and Les McCann's Swiss Movement, released in 1969. Vinnegar also performed at the Lighthouse in Hermosa Beach, California, and Diggers in East Los Angeles in the late 1950s, with drummer and pianist Don Joham along with other musicians. He moved to Portland, Oregon in 1986. In 1995, the Oregon State Legislature honored him by proclaiming May 1 Leroy Vinnegar Day.
Vinnegar died of a heart attack, at the age of 71, on August 3, 1999, in a hospital in Portland.