Milan need a point from their home game with Ajax to progress in the Champions League, as Stephan El Shaarawy and Kaka support Mario Balotelli.
It kicks off at San Siro at 19.45 GMT and anything other than a defeat will see the Rossoneri go through to the last 16.
The Dutch side are fresh from a shock victory over Barcelona, which has put them in the position to potentially qualify.
Massimiliano Allegri is still under a great deal of pressure, having won just one of his last eight Serie A games.
Balotelli starts with Ricky Kaka and El Shaarawy, the Little Pharaoh making his first start since suffering a micro-fracture.
There are surprise changes, though, as Daniele Bonera and Kevin Constant push Philippe Mexes and Urby Emanuelson on to the bench, while Sulley Muntari returns from injury in place of Andrea Poli.
The injury list includes Robinho, Ignazio Abate, Matias Silvestre, Marco Amelia and Valter Birsa.
Not on the Champions League list are Gabriel, Riccardo Saponara and M’Baye Niang.
Ajax won 2-0 at San Siro on their last visit in 2010, but that was against a makeshift Milan side that had already secured qualification.
It’s also worth noting they have not won any of their last six Champions League away games.
Kolbeinn Sigthorsson has shaken off an ankle injury for a spot on the bench, though Nicolai Boilesen, Lerin Duarte, Siem De Jong and the suspended Joel Veltman are out of action.
It’s a special game for Bojan Krkic, who had a disappointing season on loan at Milan.
Milan: Abbiati; De Sciglio, Bonera, Zapata, Constant; Montolivo, De Jong, Muntari; Kaka, El Shaarawy; Balotelli
Milan bench: Coppola, Mexes, Zaccardo, Poli, Nocerino, Emanuelson, Matri
Ajax: Cillessen; Van Rhijn, Moisander, Denswil, Blind; Klaassen, C Poulsen, Serero; Schone, Bojan, Fischer
Ajax bench: Vermeer, Van Der Hoorn, Sigthorsson, L Andersen, Hoesen, Ligeon, De Sa