Stefano Pioli's men have not won a game this season, while Milan have triumphed just once in their opening four games.
Massimiliano Allegri's side's latest defeat came in front of their own fans against Napoli, whose 2-1 victory marked the first time in 27 years that they had beaten Milan at San Siro in the top flight.
Mario Balotelli endured a typically eventful game, the striker missing the first penalty of his career, before scoring in spectacular fashion and then being dismissed after the final whistle following an argument with the referee.
The Italy international will now miss the next three games and he will join a number of first-team players on the sidelines.
Stephan El Shaarawy, Riccardo Montolivo and Kaka (all thigh) are out, as is on-loan defender Matias Silvestre (knee).
Defenders Daniele Bonera and Mattia De Sciglio, and striker Giampaolo Pazzini (all knee) are also unavailable .
Still, despite a long list of notable absentees, Allegri's men should head to Emilia-Romagna with a good deal of confidence, having done the double over Bologna last season.
Bologna have not beaten Milan since 2008, when goals from Marco Di Vaio and Francesco Valiani gave them a 2-1 win at San Siro.
Pioli's side have been in dreadful form so far this term, with their latest defeat coming at the Stadio Renato Dall'Ara against Torino, who emerged 2-1 winners.
Cesare Natali found the net for Bologna in that game, but the defender will be absent against Milan after he was shown a straight red card early in the second half.
Defender Nicolo Cherubin (foot) is still on the sidelines, while midfielder Rene Krhin and defender Frederik Sorensen are yet to return to fitness.
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