He played junior hockey in the WHL from 1972-75. After winning the Del Wilson Trophy (top goalie) in 1974-75, Oleschuk was chosen 110th overall by the Kansas City Scouts in the 1975 NHL Amateur Draft. Oleschuk spent his entire pro career in the Kansas City Scouts - Colorado Rockies organization. He never was able to duplicate his junior feats, partially because of the weak defences he played behind. He managed to get in 55 NHL games before retiring in 1984.