Bologna v AC Milan Best Betting Predictions, Cheat Sheet & Predicted Lineups

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Bologna v AC Milan
Kick Off: Wednesday 14th May at 20:00
Competition: Coppa Italia
In what is likely the most important match in the seasons of both sides, Bologna and Milan meet at the Stadio Olimpico in Rome to compete in the Coppa Italia final.
The significance of the result differs drastically in reasoning between the two teams: for Milan, it serves as a crucial pathway to achieving Europa League football next season; however, for Bologna, it’s the trophy itself that bears the most weight.
Bologna’s last major trophy came in 1974 as they scooped up the Coppa Italia in a penalty win over Palermo - the only time they’ve lifted the trophy.
Milan, by contrast, have endured more recent success, including in this competition, which they have won five times, although in the context of the nine finals they’ve lost, this record becomes significantly less impressive.
They haven’t won the competition in 22 years, with their most recent final coming in 2018 as they were destroyed 4-0 by Juventus.
⭐ Bologna v AC Milan Best Bet
➡️ Both Teams to Score in the Second Half @ 3.50 on bet365
Backing both teams to score in the second half looks a shrewd punt, and recent form backs it up. When Milan and Bologna clashed just five days ago, this exact bet landed, in keeping with both sides’ tendency to spark into life after the break.
Milan average just 0.56 first-half goals away from home, with this figure augmenting dramatically to 1.11 in the second, while they also concede more at a higher rate late on (0.83 v 0.50).
Bologna follow a similar pattern, scoring just 0.44 before half-time but 1.06 after. They’re also defensively more vulnerable in the second period (0.64 v 0.50 conceded), especially on the road, where they’ve conceded an average of 0.94 in the second half.
That second-half surge means this selection has landed in 44% of Milan’s away games (36% overall) and 31% of Bologna’s. At 3.50, this looks a high value selection.
👕 Bologna v AC Milan Predicted XI

🔍 Bologna v AC Milan Players to Watch
⚪ Lewis Ferguson
Lewis Ferguson has been a standout in the tackles market of late. Despite shifting into a more advanced role this season, the Scotsman still averages 1.9 tackles per 90 minutes. This 1+ line has landed in 12 of his last 13 starts, only missing out in a 4-0 Coppa Italia cruise against Monza, where Bologna dominated possession.
That won’t be the case against Milan. With Conceição’s side favouring pace and directness in transition, Ferguson will find himself burdened with far more defensive responsibility.
➡️ Lewis Ferguson to Make 1+ Tackles @ 1.33 on bet365
🔴 Theo Hernandez
Theo Hernandez to register a shot at 1.40 looks undervalued, particularly given his consistent output and recent positional shift.
The Frenchman averages 1.53 shots per 90, better than several Milan teammates priced shorter in this market. He’s hit at least one effort in six of his last seven outings, with that consistency extending across all competitions.
Crucially, Milan’s move to a 3-4-2-1 has pushed Hernandez into a more advanced wing-back role, perfectly suited to his attacking instincts. With added freedom to drive forward and contribute in the final third, his shot output is trending further upwards.
➡️ Theo Hernandez to have 1+ Shots @ 1.40 on bet365
📂 Bologna v AC Milan Cheat Sheet
We're all over this week's footballing action, with our expert Football Betting Predictions diving into all the action. Make sure to check out our European Football Betting Tips so you don’t miss any of our coverage.
Check out the best Bologna v AC Milan Betting Stats ahead of kick-off. We also have plenty more accumulator action for Wednesday's slate, with MLS Accumulator Tips, a Scottish Premiership Treble and Stockport v Leyton Orient Betting Tips - plus Gem Bets.
Be sure to check out our Bet Builder Stats tool too, the best freely available data source for punting on football, plus our collection of the best Free Bet Offers.
💻 Bologna v AC Milan Form and Tactics
A reasonable expectation is that this game might play out similarly to the previous clash between Milan and Bologna, which occurred last Friday.
On that occasion, Bologna kept most of the ball, averaging 53% possession. That fits with what we’ve seen this season; only Inter have dominated more of the ball than Vincenzo Italiano’s men, who average 58.5% possession.
If anything, this discrepancy is likely to further increase on Wednesday, with Milan no longer aided by playing in front of their own fans at the San Siro.
Conceicao won’t be too bothered by this, with the Portuguese coach preferring fast-paced, direct, attacking play, with a significant emphasis on the transition.
The shift to a 3-4-2-1 has aided him in pursuing this style, allowing Milan’s pacey wingbacks Hernandez and Jiminez to get further forward.
It also reduces the extent to which Leao is burdened by defensive chores, which have never been his strong suit. He bagged against Genoa in this capacity and could play a major role in proceedings.
🏁 Bologna v AC Milan Ref Watch
Referee: Maurizio Mariani
Fouls | Yellow Cards | Red Cards |
---|---|---|
24.38 | 3.69 | 0.13 |
Stats are on a per 90 basis and are taken from Mariani's 2024/25 games (32 total)
Football Predictions at Andy's Bet Club
We recommend the Best Betting Sites For Accumulators, Top Bet Builder Sites, and Weekly Free Bet Clubs, all to ensure you bet smarter when backing our tips with the Best UK Sports Betting Sites. There's a list of the best New Bookmaker Offers here.
Expert guides, such as this one, on xG In Football, are also available to help you up your punting game. To back the bets in this preview, it's worth taking advantage of this bet365 Sign Up Offer.
Free-to-play gamers should check out our Paddy Power Beat The Drop Tips and bet365 6 Scores Challenge Predictions.
* I recommend waiting for confirmed team line-ups before placing any bets.
* All odds displayed correct at the time of publishing.
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