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#3 Juande Ramos | Tottenham
Juande Ramos' managerial career was flourishing at Sevilla (where he won the UEFA Cup on consecutive occasions), and Tottenham Hotspur were quick to offer him a contract after they sacked Martin Jol in 2007. Spurs were in the relegation zone at the time and required a change in fortunes. However, they were wrong to assume that the Spanish manager would provide long-term success.
His effect in the club was immediate, with Spurs driving out of the red zone into mid-table comforts while winning the League Cup at the end of the season. However, the club soon returned to mediocrity as the new season saw Juande Ramos's Spurs picked up just two points from eight games. In October 2008, just a year after he was hired, the Spanish manager was sacked and replaced by Harry Redknapp.
#2 Andre Villas-Boas | Chelsea
It's not every day a manager moves from one club to another with a commanding €15 million fee. That, in fact, is just what Chelsea did to get Andre Villas-Boas from Porto, and even though this happened in 2011, it was a world record for a decade. The massive fee paid for him is perhaps the reason why his sub-par performances as manager hit Chelsea all the more hard.
By the close of the winter transfer window in 2012, Chelsea was struggling to get back into the top four positions in the league. After successive defeats, crashing out of the Champions League, and questionable tactics, Villas-Boas was fired. He shockingly spent only 9 months on the job.
#1 Frank de Boer | Crystal Palace
After an illustrious career as a footballer, Frank de Boer's move into management has had its fair share of disastrous moments. Although he won the Eredivisie four times with Ajax, his successes have been few and far between. His failures, however, have generally been consistent. The former Barcelona star will, in particular, want to forever forget his time at the helm of Crystal Palace.
Even though he was sacked by Inter Milan after 14 games in charge, the Eagles still thought he would be worth the chance. He was their worst mistake ever. Hired in June 2017 and fired by September 2017, de Boer lost the first four league games without his team scoring a single goal, breaking a 93-year-old Premier League record.
Jose Mourinho aptly described Frank de Boer as the worst manager in the history of the Premier League, and seeing de Boer's failure with Palace, it's hard to argue with Mourinho.
