Win or bust: The £43m game for AC Milan

The Rossoneri were among the Champions League's highest earners last season, meaning failure to reach this year's group stages could seriously hamper their ambitions
By Kris Voakes

If it feels as though AC Milan have been pretty quiet in the transfer window this summer, it is because they have.

While Philippe Mexes’ late winner against Siena in their final Serie A game of last season secured third spot and the chance to play for a Champions League place, the uncertainty of their European future has meant that the Rossoneri have had to keep a tight hold of the purse strings at a time when other superstar clubs have been throwing their weight around in the market.

More than three months on from their late, late show in Tuscany, tonight’s clash with PSV will shed light on their situation for the season ahead. And the futures of Milan and Massimiliano Allegri can surely never have been balanced on such a precipice.

The monetary rewards for Champions League participation are bigger than ever, with the Rossoneri having raked in €51.4 million (£44.3m) in prize money and commercial bonuses last season thanks to their run to the last 16. Compare that with Lazio’s return of less than €9.6m (£8.28m) for reaching the Europa League quarter-finals and it is immediately clear just how important Wednesday’s San Siro clash is to everyone associated with the club. Having already stressed the need to tighten their belts a year ago, this is not an outfit which can turn its nose up at a €50m-plus bonanza.

THE GREAT DIVIDE | Prize money and bonuses from 2012-13
Juventus Quarter-final £56.3m Lazio Quarter-final £8.28m
Last 16 £44.3m
Last 32 £5.95m
      Inter Last 16 £5.69m
      Udinese Group stage £3.45m

The need to await this tie’s outcome before spending any of the pot of gold which may be handed to them has meant that Milan have started the season in a state of flux. Saturday’s 2-1 defeat to Verona was evidently a result of the club being unable to address any of the issues which sprung up during a tumultuous 2012-13 season.

If they are not to be left taking on much-strengthened Serie A opponents with the same static defence, light midfield and potentially-incompatible forwards for another campaign, then victory on Wednesday is imperative. Mamadou Sakho, Davide Astori, Keisuke Honda and Alessandro Matri are on the shopping list, but while all four could come in with a win tonight, there is the very real possibility that none of them will arrive if they are eliminated.

If rumours around the city of Milan are anything to go by, then Allegri could well pay the ultimate price if his side are dumped into the Europa League by PSV. There has been increasing talk among informed figures over the last 24 hours that Italy Under-21 coach Devis Mangia is being lined up as a replacement should the Diavolo come unstuck in their Champions League bid.

The former Cagliari boss was given the benefit of the doubt earlier this summer having presided over a desperate late scramble for a podium position, but failure to take his men to the top table will likely see him being shown the door.

Though they go into the fixture as favourites following the 1-1 first-leg draw in the Netherlands, the manner in which Milan rode their luck for long spells eight days ago has led many to suggest that Phillip Cocu’s side are not as far behind the Rossoneri as most had predicted. Throw in the drastic need for a result for the wider health of the club, and you could forgive the Curva Sud for having an anxious tone.

At a time of so much uncertainty, the only thing that is clear is that tonight’s game is the most important one Milan will play all season.

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