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Be it Kaka running riot at Old Trafford as well as the San Siro, or a Wayne Rooney-inspired Manchester United ousting AC Milan 7-2 on aggregate in the Champions League - this fixture is never short of epic action irrespective of the venue or the competition.
Having locked horns multiple times in the past on Europe's biggest footballing stage, the two sides from Manchester and Milan meet in the UEFA Europa League round of 16 on Thursday.
While Manchester United faced a disappointing Champions League exit on the last day of group stage action, Milan had to settle for a Europa League qualification spot as they finished sixth last season in Serie A.
Well, both clubs do look revamped and back to their best level this season though. Manchester United sit second in the Premier League and come into this contest on the back of an impressive 2-0 win over rivals Manchester City.
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Meanwhile, AC Milan led Serie A for a number of weeks but currently sit second behind Inter in the points table.
An interesting piece of trivia is that this battle of the two European heavyweights has never ended in a draw since data collection began back in the late 1990s.
Manchester United have also won 5 of the last 6 meetings between the two sides, and will be hoping to make a mark early in the first leg, which should set the tone for their victory over the two-legged tie.
With that being said, here are five key battles that could decide the game as AC Milan take a trip to The Theatre of Dreams to face Manchester United on Thursday evening.
#5 Alex Telles (Manchester United) vs Alexis Saelemaekers (AC Milan)
The arrival of Alex Telles at Manchester United from Porto has not only spurred the career growth of the Brazilian full-back, but has indirectly had a huge impact on Luke Shaw as well.
Signed as a potential rotation candidate in Shaw's left-back role, Telles has had a slow start to life in England as his English counterpart has left him sidelined due to amazing performances.
But with Shaw doubtful for this first leg encounter, Telles is tipped to make his eighth appearance of the season for Manchester United. Though he has statistics to back him up (two assists in six starts), a high-profile game after a prolonged spell on the bench might give him some nerves.
Especially when he will be coming up against a dynamic winger like AC Milan's Alexis Saelemaekers this week. Saelemaekers not only contributes to AC Milan's offensive phases, but is equally involved in the defensive work as he is seen falling back whenever his team loses possession in any area of the pitch.
He is also AC Milan's third-best ranked player in terms of successful pressures in the final third - something Telles would have to deal with constantly in the ninety minutes to ensue.
It wouldn't be an exaggeration to say that Telles will be facing two right-backs on Thursday night when attacking the AC Milan goal, which could be a tedious task for the Brazilian.
#4 Mason Greenwood (Manchester United) vs Diogo Dalot (AC Milan)
Diogo Dalot seems to have found a new lease to his footballing life after switching to AC Milan, albeit on a temporary deal. As the UEFA rules allow players to play against their parent clubs, we might just witness Dalot come back to Old Trafford in AC Milan's colors this time to face parent club Manchester United.
It's a big game for the 21-year-old full-back as he will be under immense pressure to not only prove himself to his potential suitors AC Milan, but also to Ole Gunnar Solskjaer if Manchester United want to retain him from next season onwards.
Additional pressure comes in the form of Mason Greenwood on the flank. The teenage sensation from the Manchester United academy has been unbelievably good since his exploits in the 2019-20 season post the COVID-break.
His form has definitely not translated to the current season, but he is still a monster on the left flank.
What makes Greenwood and Dalot a very worthy battle this week is the two-footed nature of the pair. There is no doubt that the right-flank will be an energetic area of the pitch on Thursday as one can expect the two youngsters to go head to head in tense battles to win in the final third.
#3 Rafael Leao (AC Milan) vs Harry Maguire (Manchester United)
With Zlatan Ibrahimovic doutbful for Milan and Hakan Calhanoglu being out injured, the mantle has fallen upon Rafael Leao for delivering in terms of away goals in this battle at Old Trafford.
Although Leao may not be the strongest link in the Milan camp, he has 10 direct goal contributions in what could be termed one of his weakest seasons in recent years.
On Thursday, he goes neck-to-neck with United captain Harry Maguire, which will be interesting considering the fact that the English centre-back has struggled against pacey forwards in the past.
Leao's additional attribute is that the Portuguese striker drops deep often to get more involved in the build-up play, usually taking his marker out of position many times during the game.
History has been witness that United haven't been at their best when Maguire has been caught out of position. This could be a huge talking point ahead of this Europa League fixture.
Nevertheless, this could be a pair of players to really keep an eye on during the game as they directly pose a threat to goal-scoring action at one end of the pitch.
#2 Frank Kessie (AC Milan) vs Scott McTominay (Manchester United)
If there is one man who will be remembered by the Rosonneri fans for the 2020-21 season - it shall be none other than Franck Kessie.
The Ivorian has 9 goals and 2 assists this season which are incredible figures for a midfielder and Milan could really get some help from his goal-scoring abilities in this away leg against Manchester United.
Though most of his goals have come through penalties, his ability to bury the ball despite immense pressure is certainly commendable.
Young Scott McTominay's job on Thursday would be to contain Kessie as it stands. Paul Pogba is out injured and Solskjaer hasn't preferred Donny van de Beek and Nemanja Matic off-late for his first team roles.
McTominay might need to have the game of his life to keep the Milan central midfielder quiet as Kessie is known for his daunting late runs on the edge of the box, which could be brutal if United fail to clear the ball from the defensive third.
McTominay has been brilliant since his debut back in 2017, stepping up in big games by holding onto his position well. This will again be tested thoroughly as Milan's build-up to play has a lot of contribution from their midfield who pull the strings for Stefano Pioli.
#1 Bruno Fernandes (Manchester United) vs Alessio Romagnoli (AC Milan)
Since his arrival from Sporting CP, Bruno Fernandes has been a revelation for Solskjaer's Manchester United. A talisman on the field who brings his A-game week in, week out, Fernandes shall once again be in the headlines ahead of the Milan clash on Thursday night.
Though an advanced midfielder in the starting eleven, Fernandes is often seen in a much higher role on the pitch, thus giving United an opportunity to have two men upfront.
With that being said, Fernandes shall be a key figure alongside Anthony Martial attacking the Milan goal from the middle of the pitch - making a case for Alessio Romagnoli to be involved in many exchanges during the game.
The 26-year-old centre-back is a reactive defender rather than a proactive one, who likes to make late tackles or blocks in the game. This could tactically ricochet on him as an extra second for Fernandes could mean the ball being in the back of the net or a sublime pass threaded to take the back-line out of the equation.
Milan haven't kept a clean sheet in the last 4 meetings with Manchester United and it will be half the battle won if Pioli can take a clean sheet back to the San Siro. How Romagnoli and co. manage to keep Fernandes at bay on Thursday could be pivotal to the entire two-legged tie for sure.
