From Sir Alex Ferguson to Arsene Wenger. Jose Mourinho to Pep Guardiola. The Premier League has seen some of the greatest managers of all time dominate. But for every world class, generational manager, there have been some, to be quite honest, awful managerial appointments. Some barely managing to last a couple of months at their clubs.

In this article, we are going to look into the worst of the worst and tell you the five shortest managerial stints the Premier League has ever seen.

5 - Quique Sánchez Flores - Watford (85 days)

Quique Sanchez Flores had two stints in the Premier League at Watford. The first came in 2015 where he was quite successful taking Watford to a mid table finish and an FA Cup semi final before leaving. The second however was nowhere near as good.

In September 2019, he was brought back to the club and in his first game managed a 2-2 draw with Arsenal. This only to get battered 8-0 against Manchester City a week later.

Managing just one win in three months in charge, Sanchez Flores was sacked in November 2019 after losing 2-1 away to Southampton. A total of just 85 days in charge. Shocking!

4 - Bob Bradley - Swansea (84 days)

You may recognise the name Bob Bradley from somewhere and you would be correct to think that. Bradley was made iconic, not just for having terribly short managerial stints, but for being mocked by Soccer AM every week with the interestingly named American coach stereotype character “Brad Bobley”

That character is of course based off of the real man who was appointed by Swansea in October 2016. Originally being described by the Swansea chairman Huw Jenkins as a “long term appointment” Bradley was often criticised for his use of American slang. For example saying “PK” to describe a penalty.

Well, after managing Swansea to just two wins in 11 games and conceding 29 goals along the way Bradley was sacked. 84 days into his time at the club.

ICYMI Swansea have parted company with Bob Bradley: https://t.co/wmfZufjJ0S pic.twitter.com/McSlt0tYit

— Premier League (@premierleague) December 28, 2016

3 - Frank De Boer - Crystal Palace (77 days)

Many of you reading this may have expected De Boer to be top of this list. But trust me we have some truly awful ones ahead of him.

De Boer was made out to be an exciting appointment for Crystal Palace - despite only lasting 85 days in charge of Inter Milan before this. Unfortunately for many at Selhurst Park, it wasn’t as exciting as they would have thought.

Four games into the season Palace had four loses. And to make things worse they hadn’t scored a single goal - the first side in 93 years to start the season in such fashion.

Managing just one win in his time in charge - an EFL Cup victory against Ipswich Town - De Boer was sacked by Crystal Palace after just 77 days. Jose Mourinho later describing him as “the worst manager in the history of the Premier League.”

Maybe they should have looked a bit more into his short Inter Milan stay before appointing him.

2 - Rene Meulensteen - Fulham (75 days)

Meulensteen’s time at Fulham should be studied closely by any assistant manager or coach looking to make the managerial jump.

After being a fairly respected coach at Manchester United between 2007-2013, Meulensteen decided to move to Fulham’s coaching staff and then to becoming Fulham manager after Martin Jol’s sacking.

His time started off poorly thanks to a 2-1 loss against Tottenham however he did manage to beat Aston Villa 2-0 a few days later. Unfortunately for him, Meulensteen wasn’t seen as a long term manager by Fulham with a replacement being hired just a few months later.

In December 2014, Felix Magath was hired as Fulham manager and Meulensteen got the sack. 75 short days after he started as manager.

Rene Meulensteen lasted 30 days longer as Fulham manager than Liz Truss did as PM pic.twitter.com/tUAnJGcf3t

— Fulhamish (@FulhamishPod) October 20, 2022

1 - Les Reed - Charlton Athletic (41 days)

Before this I didn’t think it was possible to last just 41 days in a job without quitting on the spot or committing a crime but Les Reed proves that to be completely wrong.

Originally joining as assistant manager, Reed got the Charlton managerial job after Ian Dowie was sacked. His time as manager couldn’t have gone much worse. Knocked out of the League Cup by league two side Wycombe Wanderers and taking Charlton to just one win in six games.

On Christmas Eve 2006, he was sacked and replaced by Alan Pardew. The media would give Reed the name “Les Misérables” showing just how truly miserable his time at Charlton was.

And to think not long before he joined the club he would write a book titled “the official FA guide to basic team coaching.” Absolutely atrocious.

#OnThisDay in 2006: Charlton Athletic parted company with manager Les Reed after six weeks. Reed only won one of his seven league games in charge of the club. #CAFC 🔴⚪️ pic.twitter.com/BSnRkJqXYQ

— On This Day in the Premier League (@OTD_PL) December 24, 2020