A distant fourth-place finish saw the Rossoneri trail in 20 points behind champions Napoli in June, but they now start a new season against perhaps their favourite opponents.
Match preview
Ultimately frustrated by their chronic inconsistency and flaws at both ends of the pitch, Milan's 2022-23 season could not live up to events of a year previously, when they completed their climb back to the top of Calcio.
A total of 10 draws and eight defeats in the league saw Stefano Pioli's side barely sneak into Serie A's top four, and a bitter exit in the Champions League semi-finals to city rivals Inter only served to double their fans' disappointment.
Since signing off with three wins on the spin to secure fourth spot ahead of Atalanta, Milan have endured a tumultuous summer, as supposed future captain Sandro Tonali swapped San Siro for the Premier League, cult hero Zlatan Ibrahimovic hung up his boots after an emotional farewell, and club legend Paolo Maldini left under a cloud following several failures in the transfer market.
After a pre-season tour to the United States featuring defeats to Barcelona, Real Madrid and Juventus, Pioli will be relieved to return to the business of keeping a young Rossoneri side competitive at the sharp end of Serie A - several new signings should help in that regard.
With Samuel Chukwueze, Yunus Musah and Christian Pulisic among those arriving at Milanello in recent weeks, Pioli prepares his team for a first-day fixture against Bologna, who Milan last met on the opening matchday three years ago, when Ibrahimovic scored both goals in a 2-0 win at San Siro.
Under Pioli, Milan have won all three Serie A season openers to date, and as they have lost just one of their last 27 league meetings with Bologna - winning some 19 times in the process - precedent will be stacked in their favour on Monday evening.
Indeed, Bologna have failed to win even one of the clubs' last 17 encounters at Stadio Dall'Ara in Serie A, losing 12 times during that period.
Thiago Motta's side will now seek to end such a miserable sequence and earn the Rossoblu's first home win over Milan since March 2002, having intermittently impressed last term, when the ex-Inter midfielder took over just a few weeks into the season.
Sitting ninth in the final standings, Bologna were never really in contention for European qualification, but they conceded the joint-fewest goals in home matches - 14, level with Inter - and improved on three consecutive bottom-half finishes.
After some mixed results in pre-season, which ended with a 1-0 defeat to AZ, Motta's men beat Cesena 2-0 in their first competitive fixture of 2023-24, progressing to the Coppa Italia's second round thanks to goals from teenage full-back Tommaso Corazza and Dutch forward Joshua Zirkzee.
The latter may have to take up some goalscoring slack as Bologna begin life without star striker Marko Arnautovic, who made his final Rossoblu appearance in the cup before moving back to Inter, where he once had a brief stay earlier in a peripatetic career.
Though they took just one point off Milan last season and have such a terrible record versus the Rossoneri, at least Bologna can cling to the fact they have lost only one of their last 11 matches at Dall'Ara on the opening day.
Bologna form (all competitions):
AC Milan pre-season form:
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Team News
Although his international teammate Yunus Musah will miss out due to suspension, USA forward Christian Pulisic should make his Serie A debut on Monday evening, joining Olivier Giroud and Rafael Leao in the visitors' front three.
In addition to Musah, ex-Bologna boss Stefano Pioli will be missing long-term injury absentee Ismael Bennacer; Sandro Tonali's departure has left another vacancy in midfield, so two more summer signings - Ruben Loftus-Cheek and Tijjani Reijnders - may also be given starts at Dall'Ara.
While at Villarreal, only Lionel Messi and Vinicius Junior completed more dribbles in La Liga than another new arrival, Samuel Chukwueze, who is set to start on the bench.
Meanwhile, Bologna will be without Adama Soumaoro - who could be sidelined until 2024 by a serious knee injury - and there are doubts about the fitness of forward pair Riccardo Orsolini and Musa Barrow.
With Marko Arnautovic recently opting for a switch to San Siro, Joshua Zirkzee should lead the line up front while his compatriot Sam Beukema makes a first Serie A start in defence, having signed from AZ earlier this summer.
Featuring at right-back for the hosts, Stefan Posch scored six league goals last term, becoming the first defender to manage more than five for Bologna since Salvatore Fresi back in 2001-02.
Bologna possible starting lineup:
Skorupski; Posch, Beukema, Bonifazi, Corazza; Dominguez, Aebischer; Orsolini, Ferguson, Ndoye; Zirkzee
AC Milan possible starting lineup:
Maignan; Kalulu, Tomori, Thiaw, Hernandez; Loftus-Cheek, Krunic, Reijnders; Pulisic, Giroud, Leao