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Chelsea vs AC Milan: Champions League betting guide

Mike Malley
Mike Malley

The Pride of London

Fireworks entertain supporters before the UEFA Champions League Group H football match between Chelsea and Zenit St Petersburg at Stamford Bridge (Photo by DANIEL LEAL/AFP via Getty Images)

Chelsea
Fireworks entertain supporters before the UEFA Champions League Group H football match between Chelsea and Zenit St Petersburg at Stamford Bridge (Photo by DANIEL LEAL/AFP via Getty Images)

Here is your betting guide to the Champions League match between Chelsea and AC Milan from Pride of London’s gambling expert, Mike Malley.

It’s rare for the third match of the Champions League group stage to feel like a must-win, but I feel pretty comfortable saying CFC’s contest with AC Milan on Wednesday falls under that category. The Blues took only a single point from their first two games and sit bottom of Group E for the moment, so a win against the reigning Italian champions would be a massive confidence boost for Graham Potter’s men. A victory would also completely flip the qualification outlook of the group, propelling the 2020/21 champions back into contention for the knockout rounds.

There’s a legitimate argument to be made that bowing out of Europe early would be best for a squad that desperately needs consistent training time to gel with its new manager, but that sort of mindset won’t fly at an ambitious club with enthusiastic new ownership like Chelsea. The players should also be feeling confident coming off the weekend’s dramatic 2-1 victory over Crystal Palace. The Rossoneri are undoubtedly a formidable side loaded with future superstars who will pose a challenge to the pride of west London. Potter is in for his first real test as Blues’ manager.

Chelsea
Conor Gallagher of Chelsea (Photo Visionhaus/Getty Images)

The early odds on this match are pretty incredible to me, as the bookmakers at FanDuel have Chelsea favored at -150, while Milan sits at +410 on the moneyline. I have no idea why the Blues are such heavy favorites. I’ll admit that the Italian giants have struggled to replicate last season’s form so far in the 2022/23 campaign, but I would attribute that more to other Serie A sides improving rather than Milan taking a step back. The left-sided duo of Rafael Leao and Theo Hernandez is legitimately one of the best in Europe at the moment, while former Chelsea cult hero Olivier Giroud is still banging in the goals as the Rossoneri’s No. 9. Reece James and his fellow defenders will have their work cut out for them. It feels inevitable that Milan will sneak at least one into the back of the net.

I honestly wouldn’t be surprised to see a lot of goals in this continental clash of the titans. Both the Blues and Rossoneri, who ironically built their recent successes on defensive excellence, have been leaking goals so far this year. Chelsea’s record at the back is second-worst in the Premier League top six, while Milan currently boasts the worst defense among the top eight Italian teams.

Chelsea
Amar Dedi of Salzburg FC and Raheem Sterling of Chelsea (Photo Visionhaus/Getty Images)

Regardless of if these large numbers of goals are due to the opposition’s attacking quality or self-inflicted errors, it’s undeniable that both Potter and Stefano Pioli need to bring some semblance of stability to their sides’ back lines. I doubt they’ll be able to do so by Wednesday, though, so over 2.5 total goals at -120 odds seem pretty strong right now.

Official Chelsea odds (via FanDuel as of October 3)

Chelsea ML: -150

AC Milan ML: +410

Draw: +290

Over/Under: 2.5 (-120/-102)

My picks

I generally don’t like to bet against Chelsea, but I have to put it out there that Milan ML at +410 is incredible value. It’s not one of my official picks, but I’m not mad at anyone who wants to sprinkle an emotional hedge on the opponent. I will, though, take a page out of the script from the Palace match and bet the Rossoneri to score over 0.5 goals at -188 odds.

I’ll take the aforementioned over 2.5 total goals in the match as well at -120. For my final pick, I have to ride ole’ reliable, the both teams to score prop (-128 odds), for the eighth consecutive contest. Let’s hope to keep up the hot streak! Let us know on social media if our tips have helped.

Mike Malley

Mike Malley

Mike is a massive Chelsea fan and avid bettor who loves the game of football. If a match can be watched, he’ll find it (and probably put some money on it).