2. Harry Redknapp 2008-2012
At number two, Harry Redknapp is both an emotional and analytical choice. The don of gaffers enjoyed a comparatively long and fruitful tenure as Tottenham gaffer. For this piece, I’m more interested in his last year in charge, as that falls within the 10-year timeframe.
His last season as gaffer – 2011-2012 – Tottenham finished in fourth place, meaning a Champions League berth for the subsequent campaign. That was no easy feat for a side that Redknapp improved significantly during his time in north London.
Redknapp, after taking over from the outgoing Juande Ramos in 2008, led Spurs to a middling eighth place finish in the league. He then revolutionized Tottenham, taking them to perennial Champions League challengers. He led Tottenham to two fourth place and a fifth place finish in his last three years at the helm.
He won 98 of his 198 matches in charge, a 49 percent winning ratio. He also led Tottenham to an FA Cup semifinal in which Spurs lost 5-1 to Chelsea.