According to Gazzetta dello Sport, AC Milan has been unable to defeat Sassuolo in Serie A for three consecutive years, and the encounters between the two teams over the past 12 years have left many memorable moments.

The clashes between the Rossoneri and the Emilia-based side have never been straightforward. From Donnarumma's Serie A debut to the lightning-fast goal by Leão, and the continuous scoring by Berardi, these matches always have something to offer.

Meetings between Sassuolo and AC Milan are never ordinary affairs, whether at the San Siro or Mapei Stadium. Goals keep coming, and Milan fans' nightmares involving Berardi always seem to arrive on schedule. These matches are full of excitement and, most importantly, they write history. For AC Milan, Sassuolo has been almost a jinx in Serie A. The Rossoneri have failed to beat Sassuolo for three years now, and over the past 12 years, many memorable moments have occurred when facing this Emilia team: from young Donnarumma's debut to Leão's record-breaking goal, and the Rossoneri's Serie A title in 2022. Of course, there was also a humiliating 5-0 defeat at San Siro. In short, there has been joy, pain, and unresolved sporting anguish between AC Milan and Sassuolo, making their relationship more special than usual. Let us review the Rossoneri's chapter in this rivalry and revisit it through six sections, strictly distinguishing the good from the bad.

Almost every time AC Milan fans face Sassuolo, they have the same nightmare: Domenico Berardi. In just one season, he scored seven goals against the same opponent. In his career, he is their "favorite victim." In January 2014, Berardi scored four goals in 47 minutes, and AC Milan lost 3-4 in one of the most bizarre matches in Serie A history. Sassuolo arrived at that match having gone without a goal for over 400 minutes. Moreover, another event occurred within 24 hours: Allegri was sacked and Seedorf took over. In May 2015, again at Mapei Stadium, Berardi scored three more goals as Sassuolo defeated the Rossoneri 3-2.

October 25, 2015 was a special day in the career of Gianluigi Donnarumma. At just 16 years and 8 months old, the young goalkeeper from Castellammare di Stabia made his Serie A debut for AC Milan. It was Sinisa Mihajlovic who gave him the opportunity after Diego López made repeated mistakes in several matches. Mihajlovic decided to entrust the Rossoneri goalkeeping position to this bright young talent in a match against Sassuolo at San Siro. In the end, AC Milan won 2-1, but for Donnarumma, it wasn't a flawless debut. Gianluigi couldn't save perfectly when Berardi scored a free-kick equalizer.

Call him "Flash Leão." In December 2020, Rafa scored the fastest goal in Serie A history at Mapei Stadium: just 6.76 seconds from kick-off to finish. Brahim touched the ball to Çalhanoğlu, who drove forward into a Sassuolo player. The perfect path then opened for Leão to rush forward. For the Portuguese forward, facing goalkeeper Consigli was easy. After the match, Pioli said: "We had four or five plans for our kick-off strategy. Rafa's goal was pre-designed." Previously, the record had stood for 19 years: Poggi of Fiorentina held it against Piacenza in 2001 with 7.20 seconds.

On May 22, 2022, AC Milan became Serie A champions. Their 19th Serie A title was confirmed on the final day of the season at Mapei Stadium, with AC Milan winning comfortably 3-0 with two goals from Giroud and one from Kessié. Considering that Sassuolo had already secured survival and had nothing to play for, this match was merely a formality. The league title that season was largely decided by the Derby della Madonnina in February, which AC Milan won 2-1 in a comeback with two goals from Giroud. From that point on, Pioli's team won 10 times and drew 4 times in the next 14 matches—unstoppable.

In the past, AC Milan versus Sassuolo has often been a goal fest: 4-3, 3-2, 3-3, and 6-1 are just some examples. In January 2023, the Rossoneri suffered a humiliating 2-5 loss to Sassuolo in a midday match at San Siro. Défrel, Frattesi, Berardi (of course), Llorente, and Matheus Henrique all scored. It was the first match of the second half of the league season, and it started badly. Pioli's team had just suffered a humiliating 0-4 defeat to Lazio at Stadio Olimpico and drew bitterly 2-2 with Lecce. After Sassuolo came the Derby della Madonnina, which Inter Milan won 1-0.

AC Milan has not won in their last three Serie A encounters with Sassuolo, with two draws and one loss. Last year, Sassuolo won 2-0 at Mapei Stadium with goals from Berardi and Llorente. It was one of the worst performances by the Rossoneri under Allegri, particularly defensively. It was early May, and the defeat further diminished AC Milan's hopes of finishing fourth at the end of the season—a goal they missed with a humiliating loss to Cagliari at San Siro on the final day. In the previous season, the first meeting between the two teams in Milan ended in a 2-2 draw: two brilliant goals from Bartesaghi weren't enough to secure victory. In April 2024, the match in Emilia ended 3-3, with Okafọr equalizing late in the game. To summarize, AC Milan has not beaten Sassuolo in Serie A since the 1-0 victory in December 2023, when Pulisic scored. In the Coppa Italia, AC Milan thrashed Sassuolo 6-0 in December 2024 and advanced to the semi-finals with ease.

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