AC Milan's nightmare start to the Serie A season continued on Sunday when they fell to a 3-1 defeat at home to Fiorentina and had a man sent off.
Erick Pulgar put the visitors ahead from the penalty spot and Gaetano Castrovilli doubled their lead after Mateo Musacchio had been shown a straight red card for a rash challenge early in the second half.
Milan goalkeeper Gianluigi Donnarumma saved a Federico Chiesa penalty but Fiorentina got their third goal through Franck Ribery before Rafael Leao pulled back a consolation for the hosts with 10 minutes remaining.
It was Milan's third consecutive defeat in just over a week and marks the first time since the 1938-39 season that the club has lost four of their first six games in a Serie A season.
The result heaps more pressure on embattled coach Marco Giampaolo and leaves them in 16th place on six points, one point above the relegation zone.
"I take responsibility as the coach, but I go forward because I believe in my ideas," Giampaolo told Sky Italia.
"The thing that annoyed me was the team looked like it turned up to San Siro without ever having a training session together. You can lose, but not like that.
"Tonight the pressure got to them, they felt the absolute need to win and I told them to play with all the right ingredients to win, not waiting for events to happen. We had to create the events ourselves.
"Instead, the pressure weighed on us, we were tense, not reacting quickly enough and evidently feeling the pressure."
Fiorentina earned their second win in a row to lift them up to ninth place on eight points.
Vincenzo Montella's side went in front after 14 minutes when Pulgar converted a spot kick after Federico Chiesa was tripped inside the box by Ismael Bennacer.
Gaetano Castrovilli struck a second for the visitors before the break, but it was disallowed for an offside in the build-up.
Milan were reduced to 10 men after 55 minutes when Musacchio's punishment for a lunge at Ribery was upgraded from a yellow to a red card following a Video Assistant Referee (VAR) review.
Castrovilli pounced on a Donnarumma parry to smash home Fiorentina's second but the goalkeeper kept the score down by diving to save Chiesa's penalty just four minutes later after Bennacer was penalised for a second time for a foul in the area.
Ribery put the result beyond doubt with a low finish after 78 minutes and large sections of the home support decided they had seen enough and began to head for the exits.
Leao bagged a consolation as he went on a slaloming run through the Fiorentina defence before sending a low finish into the far corner.