During Grant's tenure as head coach, the Bombers welcomed the likes of Ken Ploen, Leo Lewis, Ernie Pitts, and Ed Kotowich to the team. The Bombers competed in six Grey Cup games during Grant's tenure, winning four (1958, 1959, 1961, and 1962). In 1961, the Bombers won 21–14 over the Hamilton Tiger-Cats in the first Grey Cup game to go into overtime. The Bombers and Ticats met again in the 1962 Grey Cup, with the game being postponed with 9:29 left in the fourth quarter due to zero visibility in the famous "Fog Bowl". The game resumed the next morning with the Bombers winning 28–27.