Schwarzer made his debut for Middlesbrough against Stockport County in the League Cup semi-finals on 26 February 1997. He featured in the final against Leicester City, which ended as a 1–1 draw, but was injured for the replay. He also played in the 1998 League Cup final against Chelsea, but was unable to prevent Middlesbrough from slipping to a 2–0 defeat. He was part of the side, however, who beat Bolton Wanderers 2–1 to win the final six years later, despite making an error described by BBC Sport as a "howler" which allowed Kevin Davies a consolation goal for Bolton.