Fleck made three playoffs on tour in 1960, winning at the Phoenix Open in February. He tied for third at the U.S. Open in 1960, and won his third and last tour event in October 1961, The Bakersfield Open, also in a playoff. Fleck finished in the top ten at the PGA Championship in 1962 at Aronimink near Philadelphia, a tie for seventh, then left the tour in 1963. He was a club pro in Wisconsin, Illinois, and California (Plumas Lake CC), and attempted a comeback on tour in 1970. Following the death of his wife Lynn in 1975, he qualified for the U.S. Open in 1977 at age 55, but missed the cut.