With the current crop of players, Milan were unlikely to win the Champions League as the Rossoneri have no depth, are short on alternatives in key positions and have an inexperienced Coach in Leonardo. The Brazilian Coach has been decent overall working to his best with the players available at his disposal. Against Manchester United he made a number of mistakes in terms of his selection and starting lineup as well as his substitutions.

Without taking anything away from Wayne Rooney who has been phenomenal this season, Milan could have easily put this match away if a few elements went there way beginning with the choice of starters. There is no point dwelling on whether the outcome would have been different if the necessary adjustments were made, but this could serve as a lesson which will help Leonardo and the Rossoneri in the future. In recent weeks, there have been rumours concerning Leonardo’s future with reports claiming he will be ousted at the end of the season if Milan have fail to overcome the English champions.

Below are some of the key points for reference following the  loss to Manchester United:

– Dida: The Brazilian goalkeeper is unworthy of playing on a team of Milan’s stature. The custodian has proven time and again he is prone to committing errors and his performances over the last several years have left a lot to be desired. Besides his customary blunders, Dida has become an obvious weak link in the Milan defense which other teams often target. With Christian Abbiati back, why did Leonardo pick Dida ahead of him? Abbiati is not flashy but certainly more reliable than Dida.

– Starting Lineup: All season long Leonardo has been reluctant to start Klaas-Jan Huntelaar except in emergency situations and he did score twice against Udinese but why start him now? Leonardo could have used Alexandre Pato as the striker upfront with support from Ronaldinho and with Clarence Seedorf starting as well. Seedorf is a seasoned veteran and has won the Champions League on three different teams (Ajax, Real Madrid and Milan) so surely he would be more worthy to start than Huntelaar even if it meant isolating Pato upfront. Still, Ronaldinho could have been pushed further upfront while Seedorf played on the left side of the midfield.

While Daniele Bonera was not a disaster but the decision to not start Ignazio Abate who has played many more games this season is quite surprising. Abate might not be the best equipped for the right-back position given it it not his natural position but his pace could have troubled Manchester United more.

One thing critics must grant Leonardo is the fact he has been consistent all season long in terms of his selections, faith in certain players and his rotation. David Beckham started on the bench the previous two games and while Beckham is a decent player, the pressure of the occasion might have gotten to him. Beckham is not exactly the player to seek in times of intense pressure as seen with England on a couple of occasions during the World Cup. No one is doubting Beckham’s experience, his work-rate or his desire to do well but he could have contributed more coming off the bench. At this point starting with either Mathieu Flamini or Gennaro Gattuso instead of Beckham would have been better.

If Leonardo wanted to have two strikers upfront why did he not use Filippo Inzaghi who is a goal poacher and nuisance for teams. Inzaghi can easily irritate defenders with his approach to the game and is a lethal finisher as his European scoring record can attest to. In certain games experience can trumpet age and current form. Huntelaar has not really impressed so starting Inzaghi would not have been a major risk.

– Substitutions: Those were quite critical as on one hand Seedorf scored a goal after coming off the bench while Inzaghi did miss a chance to score but he added another dimension to Milan’s attacks. The change which definitely hurt Milan was the introduction of Giuseppe Favalli for the injured Luca Antonini. At 38, Favalli is too old to be playing at left-back and while he was a decent player over his career, the former Lazio defender cannot be compared to the great Paolo Maldini. The legendary Maldini was used as a centre-back in the last few years of his career since the left-back position is more demanding in terms of speed and stamina. How can Leonardo use Favalli and why did he not opt for Frenchman Flamini who has placed in that position on a few occasions in the past? At least Flamini has the legs top cope with the physical demands of the position.

– Age Factor: Of the 11 starters and the 3 substitutes who featured against Manchester, 8 players were over the age of 30 and in such a competitive sport having too many older players can easily backfire, in particular when there are few capable alternatives on the bench.

Considering all the factors above and the 3-2 final score, can Milan overcome the deficit and turn the tie around by winning at Old Trafford to secure a spot in the next round? Keep in mind a 1-0 win will not suffice as the away-goal rule will stand to benefit the Red Devils. Milan must score at least twice and win.

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