The following season Di Matteo again proved his worth to the team, contributing ten goals and numerous assists, as Chelsea went on to claim the Football League Cup and the Cup Winners' Cup, their first European honour since 1971. In the League Cup final, again against Middlesbrough, Di Matteo scored the second goal in a 2–0 win. Di Matteo played in midfield next to Gustavo Poyet, Dennis Wise and Dan Petrescu in the 1998–99 season as Chelsea finished third. During the 1999–2000 season Di Matteo was sidelined by injury but returned late in the season to score a handful of crucial goals, including his third Cup-winning goal at Wembley, once again in the FA Cup. In a dour match, Di Matteo capitalised on an error by Aston Villa goalkeeper David James to score the winner in the 72nd minute, handing Chelsea their fourth major trophy in three years. This led Di Matteo to comment on the old Wembley Stadium saying "It's a shame they're tearing the old place down it has been a very lucky ground for me".