4. Teddy Sheringham
Like Keane, Sheringham also had two spells at White Hart Lane but few can blame him for leaving for Manchester United in 1997, where he claimed three Premier League titles before returning to Spurs in 2001.
Famed for the ‘extra yard’ in his head, Sheringham was a deadly finisher, who bagged 99 goals in his first spell at Spurs and 26 in two seasons upon returning.
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