Just when Milan fans thought they had seen everything this season, up stepped goalkeeper -- yes, goalkeeper -- Alberto Brignoli to snatch a point for Benevento, ending their 14-match losing run in Serie A and wrecking Gennaro Gattuso's hopes of a first win as boss.
Issues could have been raised before Sunday's incredible 2-2 draw. Although Gattuso deserves some leeway considering the chaos at the club, his selections raised eyebrows.
Switching to a 3-4-3 system, there were positive and negative aspects to the 39-year-old's decisions. From the highs of seeing Suso and Giacomo Bonaventura played out on the wings to the lows of Nikola Kalinic continuing to be deployed through the middle with Riccardo Montolivo at the heart of the midfield.
The Croatian international may well have got himself on the scoresheet, but ultimately it was another disappointing performance in general, and that was matched by others in the starting lineup who showed the grit and determination expected from a side managed by Gattuso, but also a lack of quality.
That was arguably the biggest question mark hanging over the Milan icon as he stepped up to the senior job, as we all know the fighting spirit that he played with for so many years at the San Siro.
However, could he match rival coaches tactically and out-think them as well as out-battle them? Judging on Sunday's early sample, he may find it as difficult as expected, albeit the freak last-gasp moment with Brignoli couldn't have been predicted by anyone.
One of the biggest criticisms of former boss Vincenzo Montella was the lack of progression and direction in Milan's play, and there was little evidence on Sunday that Milan had learned their lessons.
From aimless crosses into the box to a lack of cohesion and understanding between the attacking trident, it was a frustrating performance that involved two average goals. A win would have papered over the cracks.
It's difficult to criticise Gattuso too much this early on, as he's been pushed into this situation and the pressure is on to deliver immediate results. As he noted in his postmatch interview, it was a bitterly painful setback for him.
"It hurts, I can say that," he told the media after the game. "A stabbing would've been less painful than this goal. We are Milan and must do more, because the current level is not enough. It hurts, and we're licking our wounds."
In addition, there was also a sense of bad luck as seen with Alessio Romagnoli's sending off. Replays suggested he didn't make any contact in the challenge that earned him a second yellow card, but yet Milan were forced to play out the final stages of the game with 10 men.
Nevertheless, it's perhaps a sign of the times that the Rossoneri were desperately holding on to a lead away at Benevento, a side that had lost all 14 of their previous league outings prior to the weekend.
With a distinct lack of composure and confidence from the entire team in the latter stages, recklessly clearing their lines and inviting further pressure, they attempted to waste time on countless occasions to see out the game and ultimately failed to do so.
The draw leaves them in seventh place with a measly 21 points from their opening 15 games of the season, now 13 points adrift of the top four as their aspirations of qualifying for the Champions League look like a pipe dream.
From the positivity and optimism after Yonghong Li's takeover and the investment in the squad over the summer, to the low of being held to a draw by Benevento. It's been quite the fall for Milan this season already, and it just seems to be getting worse.
With games against Rijeka, Bologna, and back-to-back meetings with Hellas Verona in the Coppa Italia and Serie A coming up, it's hoped that Gattuso still has an opportunity to get Milan on track.
However, if the squad were given a lift by his arrival this week, the desperate and frankly bizarre nature in which they conceded so late on against Benevento will have ensured that's started to dissipate already.