Milan's downward spiral began shortly after winning the Scudetto in 2011.
The following year produced a second-place finish with many of the same players—Zlatan Ibrahimovic, Alessandro Nesta, Mark Van Bommel and Christian Abbiati, among others—leading the charge. But there were clear signs the Rossoneri were fading.
Think back to Oct. 23, 2011. Milan paid a visit to Lecce, a club that would go on to relegation with an 18th-place finish that season. This should have been a routine beatdown for Milan, but, boy, did things get complicated fast.
Guillermo Giacomazzi opened the scoring for Lecce four minutes in on a set piece, and Carlos Grossmüller sent Lecce riding a high into halftime with his 37th-minute goal to make it 3-0. Sandwiched in between those two goals was the final goal of Massimo Oddo's career. Oddo was on loan to Lecce from Milan and playing in his final season.
Things could not have gotten any worse for Milan, but there was not much hope of improvement, either.
At the break, Massimiliano Allegri made two substitutions, pulling Robinho and Massimo Ambrosini from the match in favor of Alberto Aquilani and Kevin-Prince Boateng.
Boateng scored five goals in Serie A that season. He picked a great time for three of them.
The Ghanaian led a miraculous comeback, scoring video-game goals in the 49th and 54th minutes before burying the equalizer off a set piece in the 63rd minute. Down 3-0 at halftime, Milan had drawn it level.
With seven minutes to play, Mario Yepes got on the end of a short cross from Antonio Cassano and buried a header past Massimiliano Benassi to steal the three points from Milan, putting the finishing touches on a wild second-half comeback.
That comeback was one to remember. It would be nice to forget the opponent, though. For any Milan fans who have not thought of Lecce since that day, the Salentini are currently in 11th place in the southern group of Lega Pro, the third division in Italy.
As for Boateng, he has been training with Milan the last few weeks and could make an official move from Schalke as early as January.
Relive the wild match below, then relive it through the emotional roller coaster that is Tiziano Crudeli.