Ole Gunnar Solskjaer admitted that Sunday's 5-0 defeat to Liverpool at Old Trafford was his "darkest day" managing Manchester United, and few could argue with that statement.
The Red Devils were ruthlessly torn to shreds by their arch rivals and has prompted growing calls for the club to call time on the Norwegian's tenure as boss.
While this may have been Solskjaer's darkest day, we have ranked nine of the other worst moments under Ole in what is a sobering read for any followers of the Red Devils.
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1. Manchester United 0-5 Liverpool - Premier League, 24th October 2021
Sunday's defeat was undoubtedly the lowest point in Solskjaer's tenure, with United's players looking hopelessly off the pace against Jurgen Klopp's side. The game was effectively over after Liverpool raced into a 3-0 lead by the 38th minute, before Mohamed Salah added two more goals either side of half-time to complete the rout. Paul Pogba's straight red card on the hour mark compounded the misery on a horrendous afternoon.
2. Manchester United 1-6 Tottenham Hotspur - Premier League, 6th October 2020
Before Sunday's horror show, Solskjaer admitted that this was the worst defeat of his managerial career. Jose Mourinho made the best-possible return to Old Trafford, as braces from Son Heung-Min and Harry Kane, along with a goal each from Tanguy Ndombele and Serge Aurier secured a mammoth victory. It is easy to forget that Bruno Fernandes actually gave United the lead, but Spurs were rampant in their response to secure the club's biggest-ever win at Old Trafford.
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3. Villarreal 1-1 Manchester United (11-10 on pens) - Europa League Final, 26th May 2021
This game was agonisingly close to becoming Ole's finest moment as United manager after a defeat by the finest of margins to Villarreal in the Europa League Final. An 11-10 loss on penalties to Unai Emery's side denied the Red Devils a first major trophy under Solskjaer and ensured the club would go without a trophy for a fourth successive season.
4. Sevilla 2-1 Manchester United - Europa League Semi-Final, 16th August 2020
This loss to Sevilla at the end of a COVID-disrupted 2019/20 season was a very hard pill to swallow for Solskjaer's men, with it being United's third semi-final defeat of the season following disappointments in the Carabao Cup and FA Cup respectively. Fernandes had set United on their way to the final by converting a ninth-minute penalty, but goals from Suso and Luuk de Jong ensured Sevilla prevailed.
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5. Everton 4-0 Manchester United - Premier League, 21st April 2019
United's hopes of Champions League qualification were dealt a huge blow after this heavy defeat to Everton towards the end of Solskjaer's first season in charge. The result left the Red Devils two points adrift of fourth place with four games remaining, and consigned them to a fifth consecutive away defeat for the first time since 1981.
6. Istanbul Basaksehir 2-1 Manchester United - Champions League, 4th November 2020
A goal from ex-Newcastle United striker Demba Ba and Edin Visca condemned United to an embarrassing Champions League defeat to the Turkish debutants. Anthony Martial's goal sparked hopes of a comeback, but United went home empty handed and ultimately exited Europe's premier club competition at the first hurdle, following further defeats to RB Leipzig and Paris Saint Germain.
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7. 1-1 draw with Huddersfield Town and 2-0 defeat to Cardiff City - Premier League, 5th May 2019 and 12th May 2019
These results against two already-relegated teams ensured United ended the season with the most disappointing of whimpers. The 1-1 draw away to Huddersfield mathematically ended any hopes of Champions League qualification going into the final game of the season. The Terriers were on course to register the third lowest Premier League points tally of all time, which compounded the humiliation. Meanwhile, the 2-0 defeat at home to Cardiff on the final day of the season rubbed further salt into the wound to ensure Ole's side would finish sixth - an enormous 32 points behind champions Manchester City.
8. "When you play Man City in the Carabao Cup and they put their strongest team out, you know you've gone places because that means they respect us." - Ole's comments on 11th January 2020 after Manchester United 1-3 Manchester City
The shift in power in Manchester was summed up by this quote from Ole, as he looked ahead to the Carabao Cup semi-final second leg with Pep Guardiola's side. The comments received plenty of backlash on social media, with United already 3-1 down from the first leg, while others refuted the statement itself as Claudio Bravo was included in goal and Sergio Aguero was omitted from the starting line-up.
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9. Manchester United 0-2 Burnley - Premier League, 22nd January 2020
Burnley secured their first-ever Premier League win at Old Trafford thanks to goals from Chris Wood and Jay Rodriguez. The result left the Reds six points adrift of Chelsea in the top four and with another battle to secure a top-four finish. This was ultimately achieved with a 2-0 win at Leicester City on the final day of the season.
10. Watford 2-0 Manchester United - Premier League, 22nd December 2019
United slumped to a 2-0 defeat against a table-propping Watford side that ultimately succumbed to relegation. Ismaila Sarr broke the deadlock for the Hornets with a goal of pure comedy, as his mis-hit shot bounced through David De Gea's arms and struck him on the face before going in. Troy Deeney then added a second from the penalty spot.
Topics: Manchester City, Bruno Fernandes, Liverpool, Carabao Cup, David De Gea, Europa League, Manchester United, Pep Guardiola, Premier League, FA Cup, Jurgen Klopp, Champions League, Ole Gunnar Solskjaer