Gregg played in United's first match after the disaster, a FA Cup fifth round tie with Sheffield Wednesday. United won 3–0 and went on to reach the 1958 FA Cup Final, which they lost 2–0 to Bolton Wanderers. The second goal in the final was scored in controversial fashion as Nat Lofthouse barged Gregg, and the ball with him, into the goal. United finished ninth in the league that season, as their league form declined after losing so many players in the Munich tragedy.