AC Milan failed to find a winner against the 18th place Bologna and muffled themselves to a goalless draw in the Serie A football league at Stadio Renato Dall'Ara.
Thanks to their lackluster performance, Rossoneri could manage only 0-0 draw even though they had 72% through.
As both teams failed to score a goal, the attention of the game turned towards the red card. Midfielder Tiemoué Bakayoko received his second yellow in the 79th minute for a bad foul, adding more pain to Milan camp.
Bakayoko and Franck Kessié, who also got a yellow card, will miss the match against Fiorentina on Saturday.
The Tuesday night game also marked a reunion of Milan coach Gennaro Gattuso and his counterpart Filippo Inzaghi, the teammates who were with the Italian national side that won the 2006 World Cup. They also won the Champions League in 2003 and 2007 with AC Milan.
After their elimination from the Europa League last week, Milan were struggling to convert a goal.
The result means, they are two points above Lazio, who were defeated 1-0 by Atalanta on Tuesday. The 18th-time Serie A champions won only once in their six domestic matches.