Sylvester McKinnon played with the Ironmen for 1961 to 1971. In 1961, they took second place in the Grant Park Major Tournament. From 1972 to 1979, he played with the Flamingos. In 1974, they took third place at the nationals held in Dalton, Georgia.
In 1976, they played in the nationals in Sioux Falls, South Dakota. In 1978, they played in the nationals at Marshalltown, Iowa. He played with Flash from 1979 to 1986. In 1980, they competed at the nationals in Marshalltown, Iowa. In 1982, they competed in the nationals in Aberdeen, South Dakota.
Sylvester also competed at Kelly Park and Mt. Prospect with the Ironmen, the Flamingos, and Flash. He played right field, first base, and catcher. He was selected MVP of the Grant Park Major League in 1967. In 1973, he was MVP at Cold Park.