Gennaro Gattuso recently resigned as manager of Milan following his side's failure to qualify for next season's Champions League.
Despite continuing the push to Serie A's final day, I Rossoneri were pipped to a top four spot by rivals Inter and Atalanta.
Both the Milan clubs have been way off the pace of champions Juventus for a while now. Gattuso's failure to take a significant step towards changing this in qualifying for Europe's elite competition leaves the club seeking his replacement. Here's who could do that.
It's safe to say Jardim significantly over-performed during his time in charge of Monaco. Whilst he did take advantage of a wealth of promising young talent, any sort of success in terms of trophies was never an expectation with Paris Saint-Germain being France's dominant force.
Claiming the Ligue 1 title and reaching the Champions League semi final in the 2016/17 season was a real achievement and highlighted Jardim's capabilities. However, he struggled to cope with the inevitable sale of key players like Kylian Mbappe and Tiemoue Bakayoko, consequently facing the sack earlier this season.
Monaco replaced him with the inexperienced Thierry Henry and quickly realised this dismissal was a premature one. The former Arsenal player was also sacked not long after only for Jardim to be re-appointed. He managed to rescue the side from relegation but is a manager who should be competing at the top rather than the bottom.
Not to be confused with his brother and former Milan striker and manager Filippo, Simone is the current head coach of Lazio.
The Italian was appointed in the 2016/17 season but his latest campaign will come as a slight disappointment in terms of league position. An eighth place finish would ordinarily see them miss out on Europe entirely.
Fortunately for them, I Biancocelesti were crowned Coppa Italia champions after defeating the high-flying Atalanta in the final. This victory earned them a Europa League spot in the same way winning England's FA Cup does.
Lazio striker Ciro Immobile failed to match the 29 goals he managed to score last season, but Inzaghi's style would be perfectly suited to Milan, who have typically used an attacking 4-3-3 formation throughout this season.
Like Inzaghi, Marco Giampaolo is also the current manager of a Serie A side. He guided Sampdoria to a ninth place finish, just six points and one goal worse off than the aforementioned Lazio.
However, that's where the similarities between the sides and managers end. Giampaolo has become renowned for his defensive tactics and it's easy to see why when his side only conceded four goals in their opening eight league games of this season.
A preferred formation of 4-3-1-2 provides a solid core and offers plenty of protection to the defence. Yet, Sampdoria haven't been short of goals this season either, boasting the league's top scorer in Fabio Quagliarella who found the net 26 times in 37 games. Giampaolo could be a good appointment all round.
The Serbian Sinisa Mihajlovic is the current manager of Bologna, another side who secured a top ten finish this season.
While much of the focus was on the fight for Champions League spots on the Serie A's final day, Bologna also caught the eye with an impressive 3-2 victory over second placed Napoli.
They've been capable of competing with the league's best this season, also defeating the likes of Roma and Inter as well as securing a 0-0 draw against Mihajlovic's potential suitors Milan.
But this signing looks a fairly unlikely one for a number of reasons. The 50-year-old was only appointed Bologna manager in January of this year. This, along with a previous spell in charge of AC, seems likely to hinder any possibility of a move. It's unlikely Milan will return to a manager who previously failed at the club regardless of how well he's done since.
The longer time goes on, the less likely Arsene Wenger looks to ever make a return to football management, but someone of his experience will surely attract attention from the Milan chiefs.
Wenger's latter years at Arsenal were turbulent with many fans calling for his departure way before it actually arrived, but what he achieved there can't be overlooked. He spent 22 years in north London and recorded an unbeaten season, something which has never been replicated.
If he does make a shock return to management, it's unlikely he'll be around for long, but he could provide AC with some stability nonetheless. They've had seven managers in the last five years so someone who doesn't move regularly might be just what they're looking for.
Maurizio Sarri joined Chelsea from Napoli at the start of this season and has enjoyed a fairly successful first year in England.
He's faced his fair share of criticism for being too stubborn and refusing to alter his tactics when they didn't look to be working, but he's achieved more than what was expected. The Blues have already secured a Champions League spot with the Europa League final against Arsenal still to play. A Carabao Cup final is also included in Sarri's list of accomplishments.
Since Max Allegri announced he'd be leaving Juventus, Sarri has been more greatly linked with a move to Turin than Milan. In truth, such a swift return to Italy would be a strange move, especially if it's to a club who are currently worse than his former side Napoli.