In 1981, Milton defeated future World Champion Iran Barkley of the Knights Community Center in the finals to win the 165 lb Open Championship.
Milton stopped (RSC-2)[clarification needed] Anthony Dimasso of the Nassau Police Boys Club to win the 1982 156 lb Open Championship.
In 1983, Milton defeated Mark Weinman of the Police Athletic Leagues 110th Precinct in the finals to win the 156 lb Open Championship, and captured silver at the 1983 Pan American Games.
[1] Milton won his fourth New York Golden Gloves Championship in 1984 by defeating Jesse Lanton of the Rockland County Police Athletic League in the 156 lb Open finals.
[3] The win triggered a streak which led to a bout against WBC Middleweight Title holder Julian Jackson in 1991.