After trailing 3-1, another late comeback gave the Rossoneri one consolation point, which is hardly cause for celebration.
It was another tale of a lackluster side that squandered too many occasions in front of goal and is missing its difference makers in the lineup.
Here are five things we learned from Bologna vs. Milan.
One quick look at the fact sheet and you'd think Milan truly deserved three points. They dominated possession, holding the ball 70% of the time. Out of their 18-shots, eight were directed on goal.
Statistically, Milan have kept possession as well as some of the best sides in Europe this past year, but this season they've squandered too many chances.
Milan fans might get the feeling that the team has been unlucky, as the Napoli match should have yielded three points for the Lombard side.
Mario Balotelli has scored in nearly every game he has played for Milan, but there's a risk when your entire team depends on the consistency of the flamboyant superstar.
Balotelli is still serving a three-match ban and put his team in a precarious situation when he got sent off for arguing with the referee after the Napoli match.
Apart from the goals, Balotelli gives Milan the art of improvisation, as he's a player who can change the course of the game with one stellar, unexpected move.
Alessandro Matri was useless in his second consecutive start with the Rossoneri.
The man that coach Massimiliano Allegri has been vouching for all these years has hardly looked like a difference maker, or shown anything to justify the €11m price tag.
Matri has pulled out of crucial challenges in front of goal, and hasn't looked sharp at all. His finishing has been diabolical and his link-up play with teammates leaves plenty to be desired.
It remains to be seen what Matri's role on the team will be once Stephan El Shaarawy and Giampaolo Pazzini come back from injury.
At the start of the season it seemed that a top three finish in Serie A was highly probably for the Rossoneri.
However, Milan have only managed five points in the first five games. There's a certain bleakness surrounding the club that feels even more suffocating than last season, when Milan got off to their worst ever franchise start.
The difference is that this year the top of Serie A is much stronger. Teams like Roma, Napoli, Fiorentina, and Inter are better and are all fighting for those same three spots.
Milan are now ten points behind first place Roma, and it'll take another heroic effort to get them back in the European mix.
Not upgrading the mediocre defense in the summer is coming back to bite Milan this season. They're the team that has conceded the most aerial goals since the beginning of 2012 and reinforcements in January are mandatory.
Instead of buying Alessandro Matri, the funds should have gone towards bringing an experienced defender who could bolster the backline.
The Philippe Mexes-Christian Zapata partnership has worn out its welcome, and it seems impossible for the team to truly compete when keeping a clean sheet seems like the most formidable task.