David Pleat is the only caretaker boss to make it in to this list - and that's because he's taken the role no less than three times since the Premier League started. Having been the permanent boss from 1986 to 1987 (guiding them to third place in the old First Division), Pleat has temporarily taken charge of Spurs in 1998 following the dismissal of Christian Gross, in 2001 following the dismissal of George Graham and in 2003 following the dismissal of club legend Glenn Hoddle. In those three spells, Pleat won nothing at all and his longest spell in charge - for 33 league games in 2003-04 season - saw Spurs win 12, draw 6 and lose 15 of those games.and finish 14th in the Premier League. He also has a habit of acting and portraying himself like something of a bumbling idiot, which absolutely doesn't help matters.
