 The Winnipeg Blue Bombers hired O'Shea an December 4, 2013, he became the team's 30th Head Coach in team history.In his sixth year with the team, O'Shea won his first Grey Cup as a head coach, defeating the Hamilton Tiger-Cats and ending a 29-year drought in Winnipeg with a win in the 107th Grey Cup game.O'Shea had helped establish a winning foundation for the Bombers, following four successful double-digit win seasons.