Milan have travelled to Manchester for the first of the two-legged last-16 ties, their first meeting since United humbled them 7-2 on aggregate in the 2010 Champions League.
Both sides currently sit second in their respective divisions, with United 14 points behind local rivals Manchester City in the Premier League and Milan six points off Serie A leaders and fellow San Siro occupants Inter.
One man who has more skin in the game than most for this one is former goalkeeper Massimo Taibi.
The Italian stopper spent time with both Milan and United and is now Serie B side Reggina’s sporting director.
Both teams boast excellent goalkeepers at their clubs. Gianluigi Donnarumma, 22, has been a mainstay in the Milan goal since breaking through as a teenager in 2015, while De Gea, 30, has been United’s first choice since 2011.
While Dean Henderson will deputise for De Gea on Thursday night after he travelled back to Madrid for his son’s birth, Taibi was asked to choose between the Spain international and Italy goalkeeper Donnarumma.
‘They are two great ‘keepers, but I prefer Donnarumma,’ Taibi told Football Italia.
He added on the game itself: ‘It will be an even and open game.
‘No, I don’t think so [that United are the favourites]. It will be an even game.
‘They have proved to cope well with absentees, but the same is true of Manchester United. The team that will make fewer mistakes will go through.’