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#6 Jermain Defoe (West Ham to Tottenham - £7 million - February 2004 and Portsmouth to Tottenham - £15.75 million - January 2009)
Another case of a Premier League club letting a player leave in a transfer window and scampering back to get him in the future. Spurs signed Defoe during the January transfer window of 2004, and barring one season where he played for Portsmouth, Defoe became a cult hero for the White Hart Lane faithful.
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With goals aplenty (5th highest goal scorer in club history) and mesmerizing performances, Defoe became a fan favourite and led Tottenham to the new era, although much of his groundwork materialized only after he left for Toronto FC in 2014.
Spurs fans can also thank Defoe for some of Harry Kane's brilliance as Harry Kane always looked to Defoe for advice early in his career and its safe to say most the advice seems to have worked for him.
Best season for Spurs - 2009/10 (24 goals and 6 assists)
Tottenham Hotspur were still considered minnows in comparison to Manchester United, Chelsea, Liverpool and Arsenal during this period and 6th-place finishes were par for the course.
But Defoe's heroics in the 2009/10 season inspired a Tottenham side, that still hadn't seen the break-out version of Gareth Bale, to a 4th place finish above Manchester City and Liverpool.
