After an injury to Mark Schwarzer, Roberts finished the ill-fated 1996/97 season as Middlesbrough's first-choice goalkeeper, notably playing in the 1997 FA Cup Final, League Cup final replay and the club's remaining Premier League games (Schwarzer was cup-tied for the FA Cup run anyway). He is remembered among Middlesbrough supporters for conceding a goal after only 43 seconds by Roberto Di Matteo of Chelsea in the FA Cup Final.