11 most hilarious managerial flops, with former Manchester United & Chelsea bosses

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Juande Ramos – Tottenham Hotspur

Promising in the cup competitions, but the 60-year-old couldn’t deliver where it mattered most – the Premier League.

He led Spurs to their worst ever start to a season in the 2008/09 campaign, leaving his eventual dismissal unsurprising.

Paolo Di Canio – Sunderland

The Italian’s spell was always going to end in controversy, given the temperament of the West Ham legend.

Nonetheless, he was appointed to save the Black Cats from relegation in his first season – and he succeeded in doing so – but a disastrous second season was cut short, with first-team players unhappy with constant criticism from their boss.

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