 O'Shea is a three-time Grey Cup champion as a player, having won all three with the Argonauts in 1996, 1997, and 2004.He is also a one time Grey Cup winning head coach, having won with the Winnipeg Blue Bombers in 2019, O'Shea also won the Grey Cup previously as a special teams coach with the Toronto Argonauts in the 100th Grey Cup.The Edmonton Eskimos picked O'Shea in the 1st round (4th overall) in the 1993 CFL Canadian College Draft.