Stefano Pioli’s Milan Career at Crossroads: Six “Make or Break” Matches in 2023

Very few figures in Italian football have been as relieved to hear the international bells ringing as under-pressure Milan coach Stefano Pioli. Less than two years after leading Rossoneri to their first Scudetto in over a decade, the 58-year-old tactician is staring down the barrel of dismissal.

Despite the San Siro chiefs’ futile attempts to sweep growing discontent under the rug by offering Pioli public support, it feels like it’s only a matter of time before Milan part ways with their long-serving manager. His four-year tenure has reached a ‘make or break’ point, where any potential mistake could prove fatal.

Following a comprehensive squad overhaul in the summer and a three-game winning Serie A start, Pioli seemed destined to inspire Milan to another season-long Scudetto fight. However, the wheels have come off somewhere down the road, turning the ex-Inter boss from a savior into an unwanted character. 

Heading into the November international break, Milan alternated between drawing and losing in their four league outings. Pioli’s side relinquished a two-goal cushion to draw 2-2 against perennial underachievers Lecce on the stroke of the two-week halt, casting further doubt on the Italian’s managerial credentials. 

In Pioli’s defense, he has had a massive injury crisis to deal with in the early goings. And when it looked like Milan could finally turn the corner, having welcomed Ruben Loftus-Cheek and Christian Pulisic back to the fold for their 2-1 Champions League win against Paris Saint-Germain, a new disaster struck.

Less than ten minutes into their dismal result at Via del Mare, Milan lost their standout performer Rafael Leao to a muscular problem. Captain Davide Calabria joined up with the Portuguese ace at halftime, putting more squeeze on Pioli’s selection options. 

His job will be on the line when Serie A returns to action next week, with Milan hoping to have as many injured players recovered by then as possible. Given the hectic schedule between now and the end of the calendar year, Pioli can ill-afford more injuries as we delve into Milan’s remaining Serie A fixtures in 2023.

Fiorentina (H) 25/11

Fiorentina’s visit to the San Siro next weekend will be the first of Milan’s four home league matches down the final stretch of the calendar year. Vincenzo Italiano’s side arrested a woeful three-game losing Serie A run with a 2-1 home triumph against Bologna last time out.

In doing so, La Viola became only the second team in Serie A this season to beat Thiago Motta’s team after Milan on the opening weekend. Despite recovering confidence ahead of this trip, Fiorentina’s three-game losing streak in away top-flight games against Rossoneri puts Pioli’s side in the driver’s seat.

Frosinone (H) 02/12

Inspired by Matias Soule’s sensational form, newcomers Frosinone have outperformed all expectations upon their Serie A return. Safe in mid-table after gathering 15 points in the first 12 matches, Eusebio Di Francesco’s men deserve the benefit of the doubt. A 2-0 away loss to Inter last weekend was a harsh reality check.

However, it takes nothing away from the Canaries’ impressive league start. Milan cannot take this encounter lightly, even though they’ll be odds-on favorites to maintain their unbeaten H2H record in Serie A (W2, D2), especially as this will be their final rehearsal ahead of a daunting-looking trip to Bergamo. 

Atalanta (A) 09/12

Before Inter picked their home fortress apart with a 2-1 win on Matchday 11, Atalanta had not conceded in any of their first five competitive home games this term (W4, D1). A 1-0 Europa League victory against Sturm Graz in the follow-up proved losing a battle of Nerazzurri was a one-off.

Regardless of Atalanta’s newly-developed aura of invincibility on home turf, Milan’s recent track record at the Gewiss Stadium can inspire confidence in Pioli’s corner. Barring an infamous 5-0 defeat on his first visit to this venue as a Milan coach in December 2019, his men have gone unbeaten in six of their last seven away league H2Hs (W3, D3).

Monza (H) 17/12

Milan outplayed Monza in both Serie A meetings last season, including an overwhelming 4-1 win at the San Siro. But Raffaele Palladino’s team is no idle threat, as evidenced by their respectable ninth place in the standings, having lost just three of their 12 league matches this term (W4, D5).

Unlike last year, Milan may not have a field day in the final third, with Monza conceding fewer league goals (11) than them (14) this season. Nonetheless, this is a must-win fixture in its strictest sense.

Salernitana (A) 22/12

If beating Monza is imperative, then this trip to Salernitana is a textbook definition of a ‘win or get sacked’ clash for Pioli. As the only Serie A side yet to pick up three points this season (D5, L7), the Salerno minnows entered the international break nailed to the bottom of the standings.

Not even the appointment of former Milan icon Filippo Inzaghi has turned Salernitanas’ fortunes, as he’s only amassed two points in his opening four games in charge. It would be some plot twist if he was to record his first league win against Rossoneri

Sassuolo (H) 30/12

Milan fans have had less than a year to put a dreadful 5-2 home defeat to Sassuolo behind them. But it’s not nearly enough time to get over such a painful result. Pioli’s team will have a chance to put supporters’ misery to bed when they lock horns with Alessio Dionisi’s strugglers in their last league match in 2023.

If Sassuolo’s 2-1 win at Inter in late September is anything to go by, underestimating them would be a grave mistake. Yet, they found themselves stranded only three points clear of the drop zone ahead of the international break after going winless in their last six league outings (D3, L3).  

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