Football Bet of the Day for Friday: Can Leao-Less Rossoneri Overcome Cup-Bound Rivals?

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As AC Milan prepare for a critical cup final, they first welcome Bologna to the San Siro on Friday night. While Milan's league campaign has been inconsistent, the Rossoblu arrive with a top-four finish still within their grasp, adding an extra edge to this contest.

One of our trusted experts, known for his deep knowledge of Italian football, has picked this game as Today’s Best Bet, and the selection makes plenty of sense.

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BET £10 GET £40 IN FREE BETS
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BET £10 GET £30 IN FREE BETS
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BET £10 GET £50 IN FREE BETS
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BET £10 GET £30 IN FREE BETS
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100% UP TO £50 ON FIRST DEPOSIT
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18+. Play Safe. From 00:01 on 18.10.2022. £30 bonus. New customers only. Minimum £10 stake on odds of 1/2 (1.5) or greater on sportsbook (excluding Virtual markets). Further terms apply. #Ad. 18+Only, gambleaware.org
New cust. Deposit £10+ in 7 days & bet on sports. Min odds apply. Reward = 4 x £10 Free Bets (2 x £10 Bet Builders & 2 x £10 Sports bet). Valid 7 days. Free bets not valid on e-sports & non UK/IE horse racing. 18+. T&Cs apply.
Open Account Offer – New Customers only. Bet £10 and get £30 in Free Bets when you join bet365. Sign up, deposit between £5 and £10 to your account and bet365 will give you five times that value in Free Bets when you place qualifying bets to the same value settle. Free Bets are paid as Bet Credits. Min odds/bet and payment method exclusions apply. Returns exclude Bet Credits stake. T&Cs , time limits & exclusions apply. Registration Required. #Ad. 18+ Only, gambleaware.org
New customers only. Register, deposit with Debit Card, and place first bet £10+ at Evens (2.0)+ on Sports within 7 days to get 3 x £10 in Sports Free Bets & 2 x £10 in Acca Free Bets within 10 hours of settlement. 7-day expiry. Eligibility exclusions & T&Cs Apply.
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AC Milan vs. Bologna

Wolfgang Shotten; Sports journalist at BettingTips4You

Both Teams to Score
3/4 - odds when tipped
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Reasoning
Marseille’s attacking strength through Aubameyang and Weah combined with Ajax’s away scoring record points firmly towards goals at both ends. Neither side keeps clean sheets in Europe, and with both desperate for their first points of the group stage, an open, high-intensity clash looks certain.
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Key Stats:

  • AC Milan have won their last two matches without Leao, demonstrating improved squad depth.
  • Bologna have not scored in their previous two away league matches, highlighting their inconsistency on the road.
  • The last time Bologna completed a league double over Milan was in 1940, underscoring the scale of their challenge.

Rationale

Despite a turbulent season, AC Milan have shown signs of revival in recent weeks. Under new manager Sergio Conceicao, the Rossoneri have found some stability, winning four of their last five matches. Conceicao's appointment followed the sacking of Paulo Fonseca, and while his reign began with Supercoppa Italiana glory, Milan's league form remained patchy until recently.

Their recent Coppa Italia semi-final triumph over Inter Milan has injected fresh optimism, with back-to-back league wins adding momentum. Star forward Rafael Leao, excelling in a more advanced 3-4-2-1 setup, scored in their 2-1 win over Genoa, further boosting morale ahead of their double-header against Bologna.

With their hopes of European qualification via the league all but over, Milan know that cup success next week is their best route back to the continent. A win over Bologna would not only maintain their recent momentum but also provide a psychological edge ahead of the final.

Given Milan’s recent upturn and Bologna’s travel struggles, this match could favour the home side. Milan’s new shape has brought stability, with their defence looking more robust and their attack beginning to click. Bologna, meanwhile, have struggled for goals away from home, failing to find the net in their last two trips. With both teams carrying cup distractions, Milan’s deeper squad and home advantage should tilt the balance in their favour.

Best Bet: AC Milan to Win and Under 2.5 Goals


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Luca Semproni
Luca Semproni was born in Italy and loves Italian football to the core. A well-known Youtuber in the tipping space, he has collaborated with BettingTips4You for several years, providing great tips, especially on the Italian football and European Cups. A disillusioned Roma fan!