2. Teddy Sheringham
Main Position: Striker. Time With Spurs: 1992-1997, 2001-2003. Teddy Sheringham is a Tottenham legend. With Spurs, he was the Premier League's top scorer in his first season (1992-93) following his move from Nottingham Forest. He was also Spurs' top scorer in a further four seasons over the following ten years. Said to have such a great footballing mind that it granted him an extra couple of yards against an opponent, Sheringham's ability to score goals was equalled by his ability to hold up the ball beautifully and always find the right pass. Sheringham formed formidable partnerships with players like Jurgen Klinsmann, Chris Armstrong and Robbie Keane and made nearly 250 league appearances for the Spurs in his two spells with the club. He was a losing finalist for Spurs in the 2-1 defeat to Blackburn in the 2001 League Cup. He is the 9th highest Premier League goalscorer of all time with 147 goals - 98 of which were with Spurs - and Spurs' 9th highest scorer of all time as well. He left for a highly successful spell with Manchester United in 1997 before returning
on a free transfer in 2001.