he moved on to leicester city in august 1998, for a fee of £2 million. he was part of the team that won the 2000 league cup, beating tranmere rovers 2–1 at the wembley stadium. during his time with leicester, sinclair developed an unfortunate reputation for scoring own goals. this was caused initially by two own goals in consecutive weekends in 1999. the first was a great leap at highbury to give arsenal a 2–1 win. he managed to refrain from putting through his own net against coventry city the following wednesday, but then scored another at home to former club chelsea, where he beat tore andré flo to the ball to smash it into his own net and lose leicester their one-goal lead. the importance of these goals was accentuated by the fact that both came in the last minute of the match, and both caused leicester to drop points, although it wasn't enough to prevent him from remaining a first team regular.