After winning two Tippeligaen titles with Molde, Ole's Premier League return with Cardiff underwhelmed as he was unable to prevent them from relegation.
A poor start in England's second-tier saw Ole part ways with Cardiff and return to his native to coach Molde for a second time.
He remains as manager and is on course to guide the club to its joint-highest position since Sir Alex Ferguson retired.
Rather than being limited to making signings like David Moyes, or being heavily backed like Louis van Gaal and the Special One, Solskjaer was given a different remit - buy youth, develop players and create a new era for Man United.
Wales international Daniel James was the first signing by Solskjaer, arriving from Swansea City in the 2019 summer window. The winger joined for a fee of £15million.
James got off to an electrifying start to his career at Old Trafford as he bagged three league goals in his first four games for the club. This included a debut goal against Chelsea in a 4-0 win after coming on as a substitute.
The goals dried up from that early season breakthrough as James had to wait seven months for his next goal. That meant ended the season with just four goals and there were concerns as to whether he was clinical or good enough to play for the club.
James remains an exciting prospect but he will have to improve even more if he is to remain at Man United.
Man United brought in Aaron Wan-Bissaka from Crystal Palace for a fee of £50million in the 2019 summer window. The right back was rated as one of the most talented full backs in the league at the time of the signing.
Wan-Bissaka will remain a key member of Man United's resurgence in the league and cup competitions.
After chasing the centre back all summer long, Man United finally completed the signing of Harry Maguire from Leicester City in 2019. The defender joined for £80million - a world-record fee for a defender.
Many thought Man United had spent way too much money on Maguire, with Virgil van Dijk costing £75million in comparison.
Maguire was named club captain following Ashley Young's departure to Inter Milan in 2020 and played every minute of Man United's 2019/20 campaign.
Maguire has faced criticism since arriving though after making big errors that have led to goals. It has even seen fans and media alike question his credentials to lead the club back to the big time. The jury remains out as to whether he'll be a success.
The best signing since Fergie. Bruno Fernandes signed from Sporting Lisbon in the 2020 January transfer for an initial fee of £47million - which could rise to £67.6million.
It looks as if he has saved Ole his job with his performances inspiring the team to a third-place finish in the 2019/20 Premier League.
Fernandes - who notched up 12 goals in 22 games - also made history by being the first player to win the Premier League Player of the Month award four times in a calendar year. The impact he has had at Old Trafford has been nothing but sensational.
Fernandes has continued his fine form from last season and has scored more than 20 goals.
Donny van de Beek
Highly-rated Netherlands international Donny van de Beek joined Man United as the club's first signing of the 2020 summer window.
Van de Beek's impressive performances for previous club Ajax in the Champions League likely alerted Man United to fight for his signature.
Van de Beek scored on his debut in a 3-1 defeat to Crystal Palace and has not scored a goal since that strike in September. The midfielder has struggled for any real opportunities in the Man United side this season.
It may already be time for him to leave.
Left back Alex Telles was signed from FC Porto for a relatively low fee of just £15.4million in 2020. The signing was one seen as providing healthy competition to Shaw.
His career at Man United has regressed since testing positive to Covid-19 and with Shaw in brilliant form this season and a trusted member of the first-team, Telles looks like he will have to settle for the bench.
Edinson Cavani joined Man United on a free transfer in 2020 after his deal at Paris Saint-Germain expired.
He scored his first goal for the club in a 3-1 win away to Everton and has scored six more goals in all competitions since. This included a match-winning brace to secure Man United all three points against Southampton.
The Uruguay international has been a valuable addition to the squad but his time looks like it will be up at the end of the season with Boca Juniors a likely destination.
Teenage winger Amad Diallo was signed from Atalanta for a hefty fee of up to £37million despite making just three appearances before the move.
Diallo remained at Atalanta for the first half of the 2020/21 season to allow time for a work permit to be sorted.
He joined up with the Man United team in January 2021 and was given the number 19 jersey. Diallo made his senior debut for Man United coming on as a substitute in a 4-0 Europa League win over Real Sociedad.
He is expected to remain in the first team squad for the remainder of the season and will seek more opportunities in the coming months.
Diallo is definitely viewed as one for the future and Man United fans will believe they have another gem at their disposal.
Facundo Pellestri was another teenage winger bought in the 2020 summer window. Pellestri joined from Uruguayan side Penarol for a fee of £9million.
Pellestri was loaned out to La Liga side Deportivo Alaves in the 2021 January window in the hope of getting regular first team football.