The 1998-99 season was a mighty success for Spurs, they managed to finish in a respectable 11th position, and however it was their league cup form which impressed the fans the most. Tottenham were outstanding in reaching the final as they met Leicester City at Wembley. Spurs needed to rely on an Alan Nielson goal in injury time to win the trophy. Spurs were highly impressive in the FA Cup as well, reaching the semi finals, only to lose out 2-0 against Newcastle in the semi finals.
Spurs finished tenth in the premiership at the end of the 1999/2000 season, after the triumph of league cup victory the previous year, Spurs crashed out of the league cup in the forth round, losing 3-1 to Fulham. They also went out at the first hurdle of the FA Cup as they were thrashed 6-1 against Newcastle.
Tottenham finished 12th in the 2000-2001 season, the departure of Sol Campbell did not help Spurs, however Teddy Sheringham returned to the club and made an immediate impact. Spurs were in decent form in the FA Cup as they reached the semi finals; however they were eliminated by the hands of their arch enemies, Arsenal, losing 2-1 at Old Trafford.
Tottenham improved during the 2001-02 season, an impressive FA Cup run ended by defeat against Chelsea. Spurs were outstanding in the league cup as they reached the final, however they lost the final 2-1 at the hands of Blackburn. Tottenham also finished ninth in the premiership which was an improvement of three positions from the previous season.