6) Tim Sherwood
Tim Sherwood was appointed as Spurs’ boss after the departure of Andre Villas-Boas. His appointment was on a temporary basis but was supposedly given an 18-month contract. He was sacked despite having the best win percentage of any Spurs boss ever following a couple of heavy defeats to major Premier League sides. He was thrashed by teams like Chelsea and Liverpool which indicated that they are not quite at the Champions League standard yet. His playing style was also not very attractive.
5) George Graham
Having been affiliated with Arsenal for a long time as a player and as a coach, Spurs fans were unhappy with his appointment as their manager in 1998. He did win the league cup with the club but his team finished mid-table in 1990-00 season and had a poor start to the next one and eventually got sacked by the club for reportedly having leaked the club’s private information to the press. Fans mostly disliked him for his very unattractive playing style.
4) Glenn Hoddle
With a win percentage of only 48.08 % and no title in his two-year tenure with the club, he is surely among the worst Tottenham managers ever. Although the playing style of the team was better under him than the previous boss George Graham but the results were awful. They were sitting in the relegation zone in 2003 when Glenn was sacked and his team had also finished mid-table in the previous two successive seasons.