Clarence Seedorf's Milan were eliminated from the UEFA Champions League in midweek as they slipped to a humiliating 4-1 defeat at the hands of Spanish side Atletico Madrid in the last 16 second leg, resulting in a 5-1 aggregate scoreline.
That humbling loss effectively ends Milan's season, the 18-time Italian champions are mired in mid-table, nine points adrift of a European place, and appear to have little to play for in the remaining months of the campaign.
And Seedorf's men now meet the challenge of one their former heroes in Donadoni, who is overseeing a remarkable transformation at Parma.
Former Italy boss Donadoni won six league titles and three European Cups in his two spells with Milan but finally looks to be restoring his reputation as a coach with his current club.
Parma finished 10th last term but are now in the running for a return to European competition following a superb run of form.
Donadoni's men have not tasted defeat in the league since November and are just one point behind Milan's arch rivals Inter in the race for a place in next season's UEFA Europa League.
The visitors' form is in stark contrast to that of Milan, who approach the game on a run of four defeats in their last five games in all competitions.
Former Napoli boss Donadoni will have little regard for his former side's struggles at the weekend, however, as Parma seek to replicate the 3-2 win they earned in the reverse fixture last October.
But history is very much on Milan's side given Parma's miserable record against them at San Siro.
Parma have not beaten Milan at San Siro since the 1999 Supercoppa Italiana, when goals from Hernan Crespo and Alain Boghossian gave the Emilia-Romagna club a 2-1 success.
Milan's last league home defeat to Parma came in 1996, but that 18-year run will likely come to an end if Donadoni's side can continue to produce the form that has seen them emerge as European contenders.
The in-form visitors will have almost a full complement of players to choose form in their quest to end the long wait for an away win at Milan, with Italy international Gabriel Paletta Parma's only absentee due to suspension.
Mattia De Sciglio is banned for Milan, while forward Stephan El Shaarawy is still on the sidelines as he recovers from a foot injury.
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