In contrast Greenwood's career has tailspinned towards oblivion, leaving him shunned by clubs in England, and 20 months without a competitive game.
And yet both have ended up in Spain and when they meet tonight in the modest surroundings of Getafe's 16,500 capacity stadium they do so on an almost equal footing – at least in as much as Bellingham has been Real Madrid's best player this season, and Greenwood can stake a claim for having been Getafe's.
There was barely a trickle of clubs trying to sign Greenwood last summer with only interest from Lazio likely to prevent Getafe from taking him on a season's loan.
Mason Greenwood is rebuilding his career with Getafe following his Manchester United exit
Greenwood has six goals and four assists in 17 starts for the Spanish club so far
But he isn't LaLiga's best-performing Englishman with Jude Bellingham in exceptional form
But after six goals and four assists in 17 starts it is likely to be a very different story this summer, even more so if the Manchester United loanee turns on the style again against Bellingham's Real Madrid.
Getafe are busy on deadline day trying to sell striker Enes Unal to Bournemouth for as close as possible to his 40million euros [£34m] release clause. That would give them some financial leverage to keep Greenwood into next season.
But with various clubs in Spain and Italy watching the situation closely they are unlikely to be able to compete.
The Greenwood effect at Getafe – they were a hard watch last season as they battled relegation – is all too evident.
They are 10th having played a one fewer game and they are in with a chance of making the European places for the first time since 2019.
Greenwood has also played a big part in Getafe centre-forward Borja Mayoral having the season of his life – he is tied on 14 goals with Bellingham and Girona centre-forward Artem Dovbyk at the top of the scoring charts.
Getafe have been pleased with his attitude too. When he joined, the club's fitness coach Javier Vidal set out a meticulous plan for him to return to his physical peak after so long without playing and after a gradual increase of minutes per match that seems to have born fruit.
He has worked with a Spanish teacher to at least learn enough of the language to be able to understand the jokes flying around in the daily squad breakfasts at the training ground.
Bellingham celebrates his goal in Real Madrid's 2-1 win over Getafe earlier in the season
Manchester United could gain a substantial transfer fee for Greenwood in the summer
And his father Andrew has been there to observe his training sessions. Manchester United have also closely monitored progress.
According to Getafe president Angel Torres, United will not be the only ones to benefit financially if he gets a big move in the summer.
Torres says Getafe agreed on taking a 20 per cent share of the player, instead of paying a loan fee for him, and so will be entitled to a share of his transfer fee.
He has impressed rivals too. After a good showing against Atletico Madrid earlier in the season Antoine Griezmann told Spanish television: 'Greenwood caused us a lot of problems; we couldn't stop him'.
No one tops Bellingham though. He remains head and shoulders the star of the season so far in LaLiga.
That would be the case even without his extraordinary goal return. He has more than filled Zinedine Zidane's No 5 shirt in the best first season anyone at Madrid has seen from a new signing in years.
He missed Madrid's weekend win over Las Palmas so comes back into the team for Thursday night rested and ready to pick up again from his performance against Almeria two weeks ago when he carried Madrid to victory scoring a penalty in the 3-2 win.
Bellingham will undoubtedly be crucial to Gareth Southgate's England at Euro 2024
The two have not been on the same pitch in Spain yet. When the sides met in early September Bellingham scored a late winner in another Real Madrid comeback.
Greenwood's first appearance came in Getafe's next game following an international break two weeks later.
They have crossed the same match official however. Jorge Figueroa Vazquez has clearly learned some English as he has climbed the ranks of refereeing in Spain.
He told Bellingham (in English) 'be careful with me' while pointing in his face in a Real Madrid win over Villarreal.
And a few weeks later he sent Greenwood off claiming the player had said: 'F**k you' to him. Greenwood told his coach and team-mates that he had only said 'F**ksake' as he turned away from the referee upset that he had not been given a foul.
In support of him one team-mate, Juan Iglesias, tweeted: 'If anyone finds a video where he says 'F**k you' I'll buy them dinner.' The red card was rescinded on review.
Jorge Figueroa Vazquez sends Greenwood off during Getafe's game with Rayo Vallecano
Vazquez also had stern words for Bellingham during Real's match against Villarreal
Bellingham and Greenwood's paths also crossed in the Spanish media just after Greenwood signed when Getafe coach Jose Bordalas said: 'Greenwood has a friendship with Bellingham and advised him to come to the Spanish league.'
In a subsequent press conference he rectified those comments saying: 'I wanted to clear up a misunderstanding. I said that Mason Greenwood came to Getafe because he had spoken to Bellingham. It has been made clear to me that this was not the case. I apologise.'
Clearly Madrid had been in touch with Getafe to prompt the rectification, prompted in turn by Bellingham's camp not happy with the incorrect assertion originally made by Bordalas.
It will be interesting to see if the two speak before, after or during the game.
And to see who comes out on top in a peculiar derby match set to be dominated by two of the most talented English footballers to have emerged in recent years – one on top of the world; the other trying to lift himself away from the bottom.
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