Last season they lost in the semi-finals of the FA Cup, League Cup and Europa League, while the season before they went out in the Champions League quarter-finals
Having been part of Alex Ferguson's Manchester United trophy-winning machine, Manchester Unitedknows exactly what is expected from the man in the Old Trafford managerial hot seat.
Battling for the Premier League runners-up spot and reaching the latter stages of cups does not really cut the mustard. Which is why United's feeble FA Cup quarter-final defeat at Leicester City on Sunday was so surprising.
There were mitigating circumstances in Solskjaer's team selection, chiefly a tough Europa League last-16 assignment three days earlier in Milan which they successfully navigated, but it still felt like a massive opportunity wasted.
Solskjaer left the likes of talisman Bruno Fernandes, in-form Luke Shaw and the reliable Scott McTominay out of his starting lineup and his side were outplayed in a 3-1 loss.
Had Solskjaer already gathered some silverware since taking charge on a full-time basis two years ago, or had a chance of catching runaway Premier League leaders Manchester City, he could perhaps be excused for gambling at Leicester.
But the defeat means United are gaining an unwanted reputation as a team that fails to deliver.
Last season they lost in the semi-finals of the FA Cup, League Cup and Europa League, while the season before they went out in the Champions League quarter-finals.
While Solskjaer can rightly point to signs of progression, the fact the trophy cabinet is gathering dust does not sit well with the fans and presumably the hierarchy who last celebrated a trophy when Jose Mourinho landed the Europa League in 2017.
"I am demoralised a little bit as a Manchester United fan as I thought (the FA Cup) was a really good one to go for," Solskjaer's former United team mate Gary Neville told Sky Sports.
Victory would have set up a semi-final against a woefully out-of-form Southampton side and a chance to go head-to-head with either Chelsea or Manchester City in the final -- the sort of high-profile game United crave.
Instead, all their eggs are now in the Europa League basket. They face Granada in the last eight but could then come up against either Ajax Amsterdam or AS Roma in the semis so there are no guarantees of success.
The only reason United are in the Europa League is because they bowed out of the Champions League in the group phase after a shambolic defeat by RB Leipzig.
Solskjaer insists he had no regrets about rotating his team at Leicester, where Paul Pogba and Donny van der Beek both started, saying the likes of Fernandes had to be rested.
"Every team selection has reasons behind it, Bruno has played lots of football -- he broke all his records physically on Thursday. He is a human being, he's played a game every three or four days," Solskjaer said.
Top players love nothing more than winning silverware though and Ferguson was prepared to flog his top performing players week after week when United won the treble in 1999.
Likewise, Jose Mourinho rarely left out his key Chelsea men while collecting trophy after trophy at Stamford Bridge.
Neville said Solskjaer needed to win a trophy.
"Of course, finishing second would be the priority at the start of the season, but winning a trophy with that would be a real priority and now they only have the Europa League left," he said.
"I genuinely believe that that group of players need to win a trophy under Ole. Also, there comes a point when if you are going to catch Manchester City, you have to beat them in a big game in a big competition."