Ole Gunnar Solskjaer will look to end his semi-final hoodoo when he takes on Roma on Thursday night, with the Manchester United boss yet to reach a final since his return to Old Trafford.
Solskjaer was appointed as caretaker boss in December 2018 following the sacking of Jose Mourinho, with it being made permanent three months later.
Whilst Mourinho is not remembered fondly by many Manchester United fans, he was the last man to lift silverware for the Red Devils, claiming the Europa League and EFL Cup in 2017.
Solskjaer will want to end his torrid run in semi-finals when he welcomes Roma in the Europa League on Thursday night, with the semi-final second leg taking place in Italy next week.
But first Mirror Football looks back on Solskjaer’s last four attempts to make a final and asks whether it will be different this time around.
Carabao Cup – January 2020
Solskjaer’s first semi-final heartbreak came at the hands of their closest rivals, Manchester City.
United actually won the second leg 1-0 thanks to Nemanja Matic’s brilliant low drive into the bottom corner but progression was always unlikely after City blew United away in the opening 38 minutes of the first leg.
An excellent strike from Bernardo Silva, Riyad Mahrez’s rounding of David De Gea and an own-goal from Andreas Pereira inside the first half was the least City deserved, although Marcus Rashford’s consolation did give United hope going into the second leg.
FA Cup – July 2020
David De Gea endured an afternoon to forget against Chelsea as his two errors either side of half-time helped Chelsea to a 3-1 victory.
In first-half injury-time he was unable to get a strong enough hand to Olivier Giroud’s flick and the break did little to help the goalkeeper, as he allowed Mason Mount’s long-range effort to squirm underneath him.
A Harry Maguire own-goal with 16 minutes remaining all-but secured Chelsea’s progression, as Bruno Fernandes’ penalty late on did little to lift the spirits of the dejected United fans.
Europa League – August 2020
This should have been the game where United’s semi-final heartbreak stopped, as Bruno Fernandes’ penalty gave them the perfect start against Sevilla.
Former Liverpool forward Suso did equalise before half-time but in the second period United wasted a series of good opportunities, with Anthony Martial denied by Yassine Bounou on several occasions.
And they paid the price with 12 minutes remaining when Luuk de Jong made it 2-1 and continued Sevilla’s remarkable record in the competition.
Carabao Cup – January 2021
New season, same old problems for United.
They may have had a goal disallowed with the scores at 0-0 but City had already had two goals chalked off before they finally took the lead in the second half, as John Stones scored his first goal in three years.
City didn’t cement their place in the final until seven minutes remaining but they had all but closed the game out by that point and could have won by more.
What has Solskjaer had to say this time around?
It’s hard to argue that United have not progressed under Solskjaer but by his own admission, now is the time to prove it by securing their first silverware in four years.
“It will be a dream come true the day I can lift a trophy for this club as a manager, of course,” Solskjaer said this week.
“That’s what we’re building for. We’ve been close, we’re building step by step but take the next step. It’s ifs and buts and this and that. You always talk about that.
“But for this team and myself, our ambition this season is to finish with lifting a trophy and being able to celebrate. I know how much that can mean for a group moving forward.”