Gascoigne left Scotland to join Middlesbrough for £3.45 million in March 1998, where former England teammate Bryan Robson was manager. His first match was the 1998 Football League Cup Final defeat to Chelsea at Wembley, where he came on as a substitute. He played seven games in the First Division, helping "Boro" into the Premier League as runners-up to Nottingham Forest at the end of the 1997–98 season.