Stefano Pioli's side finished sixth in Italy's top flight last season to secure a spot in the qualifying rounds of the Europa League, while Bologna ended the campaign in 12th position in the table.
Milan have not yet started their Serie A campaign, but the Italian giants booked their spot in the third qualifying round of the Europa League with a 2-0 success away to Shamrock Rovers on Thursday night.
Pioli's side will take on Norwegian side FK Bodo/Glimt in the next round of the European competition on September 24, with the winner of that match knowing that they need just one more victory to book their spot in the group stages, which is said to be worth around €15m (£13.8m).
Milan have not finished higher than fifth in Italy's top flight since claiming third in 2012-13, and the fact that they were 17 points off champions Juventus last term is an indication of the ground that they need to make up.
Sandro Tonali has been the club's major incoming this summer, with Milan beating a host of clubs to the signing of the 20-year-old, who made his debut in the Europa League on Thursday.
I Rossoneri will be determined to get their league campaign off to a positive start on Monday, and they have won eight of their last nine Serie A games against Bologna, remaining unbeaten in the process.
Bologna, meanwhile, finished 12th in Italy's top flight last season, winning 12, drawing 11 and losing 15 of their 38 matches to claim 47 points, 12 points clear of the relegation zone.
The Red and Blues, who are seven-time Italian champions, have largely been a bottom-half side in Italy's top flight since securing promotion back to this level for the 2015-16 season.
Bologna ended last season with a 1-1 draw at home to Torino, but they have played two friendly matches since then, beating FeralpiSalo at the start of the month before drawing with Virtus Entella last weekend.
AC Milan form (all competitions): W
Bologna pre-season form: WD
Tonali was only a substitute in the Europa League and that is again expected to be the case here, with on-loan Real Madrid attacker Brahim Diaz also likely to start on the bench.
As for Bologna, Gary Medel is suspended due to the booking that he picked up on the last weekend of the 2019-20 campaign, although a hamstring problem is likely to have ruled the Chilean out regardless.
There are not expected to be many surprises in the away side's XI on Monday night, with Musa Barrow and Roberto Soriano likely to be selected in support of Rodrigo Palacio, while De Silvestri should debut at right-back.
AC Milan possible starting lineup:
Donnarumma; Calabria, Kjaer, Gabbia, Hernandez; Kessie, Bennacer; Calhanoglu, Castillejo, Rebic; Ibrahimovic
Bologna possible starting lineup:
Skorupski; De Silvestri, Danilo, Tomiyasu, Denswil; Svanberg, Schouten; Barrow, Soriano, Orsolini; Palacio
We say: AC Milan 2-0 Bologna
Thursday's Europa League clash with Shamrock Rovers could actually help Milan in this match as they have had the chance to secure some competitive minutes. Bologna's recent record against the 18-time Italian champions is really poor, and we fancy the hosts to pick up all three points in this game.