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Chelsea and AC Milan will face off for just the sixth time in history as the two sides meet in 2022/23 Champions League Group E play.

The Blues are shockingly bottom of the group standings after two matches, losing to Dinamo Zagreb in Thomas Tuchel’s last game in charge before a home draw with RB Salzburg. Failure to win at home against Milan on Wednesday would put Chelsea’s chances of advancing in serious jeopardy halfway through the group stage.

AC Milan, meanwhile, rest atop their Champions League group and they are also mounting a serious domestic title defense in Italy’s Serie A. They are fifth in the league table in Italy, but sit just three points behind leaders Napoli and Atalanta.

A potential winner at Stamford Bridge could swing the tide of the Group E standings considerably, with the hosts reenergizing their chase for a knockout place spot, or the Italian visitors taking firm control of the group.

MORE: Latest Champions League group standings

Chelsea vs. AC Milan betting odds

Despite sitting bottom of the group without a win, Chelsea are considered heavy favorites by the bookmakers in this match. It’s a surprising differential for two teams trending in directions that are opposite their odds, with the Blues especially difficult to judge while still in the very early days of Graham Potter’s managerial tenure.

The oddsmakers, meanwhile, are undetermined how the game will look, with the odds on ‘both teams to score’ split almost evenly between “yes” and “no” responses, while the 2.5 goals total is also a nearly even divide.

Caesars Sports
Interaction
SkyBet
Chelsea win -145 1.65 4/6
Draw +290 3.89 14/5
AC Milan win +390 4.66 4/1
Both teams
to score Y / N
-120 / -110 1.75 / 1.85 4/5, 10/11
Over / Under
2.5 goals
-125 / -105 1.82 / 1.92 4/5, 10/11
Chelsea -0.5 -140 1.68
AC Milan +0.5 +110 2.15

Chelsea vs. Milan recent history

  • Chelsea vs. AC Milan all-time record: Chelsea 1 win, AC Milan 1 win, 3 draws

Shockingly, these two teams have only met five times in history, across two total matchups, and it’s impossible to separate the sides. Literally, it required a coin flip.

Most recently, the two sides matched up in the 1999/00 Champions League group stage. Ultimately though, AC Milan would finish bottom of the group with six points, while Chelsea and Hertha Berlin would advance.

The first time they matched up was in the Round of 16 of the 1966 European Fairs Cup, also known as the Inter-Cities Fairs Cup, widely considered the predecessor to the UEFA Cup, which ultimately became the Europa League. The two teams drew 3-3 on aggregate across the two legs, at which point a replay was contested. The replay finished in a 1-1 draw, and this was before the days of penalty shootouts, so a coin flip saw Chelsea advance.

Chelsea vs. AC Milan last 5 matches

Date Competition Result
Oct. 26, 1999 UEFA Champions League
Group Stage
AC Milan 1-1 Chelsea
Sept. 15, 1999 UEFA Champions League
Group Stage
Chelsea 0-0 AC Milan
Mar. 2, 1966 European Fairs Cup
Round of 16 replay
AC Milan 1-1 Chelsea*
Feb. 16, 1966 European Fairs Cup
Round of 16 second leg
Chelsea 2-1 AC Milan
Feb. 9, 1966 European Fairs Cup
Round of 16 first leg
AC Milan 2-1 Chelsea

* Chelsea advanced in the competition on a coin toss

Chelsea vs. Milan prediction

Quite honestly, the odds disparity between these two teams is hard to just ignore. It’s shocking that Chelsea, who sit bottom of the group and have looked shaky in the Premier League, are minus-odds favorites in this match against a very strong Italian side.

Yes, new manager Graham Potter should bring the Blues up from their lows a few weeks prior, and the introduction of Pierre-Emerick Aubameyang is a major plus for the attack. But even given those net positives, the Blues were flattered in their 2-1 victory against Crystal Palace over the weekend, needing a late Conor Gallagher winner to skate by.

AC Milan have been far from flawless, but they earned a hard-fought victory over Inter a month ago and thumped Empoli last time out. The creative duo of Rafael Leao and Charles De Ketelaere has been incisive, with veteran Frenchman Olivier Giroud leading the line in place of the injured Zlatan Ibrahimovic. They’ve all done enough to equal their 16.13 xG total in league action, which is second-best in the league.

The Italian side is spectacular value in this match.

  • Moneyline lean: AC Milan (+390 on Caesars)
  • Against the Spread (handicap) lean: AC Milan +0.5 (+110 on Caesars)
  • Scoreline prediction: Chelsea 1-2 AC Milan

Chelsea vs. AC Milan best bets & expert analysis

Chelsea vs. AC Milan best bet: Milan +0.5 team goals

  • Pick: AC Milan +0.5 goals (+111 on Caesars)

The odds in this match are so skewed towards Chelsea, it’s almost fishy.

AC Milan are just the better team right now, even with the injuries they’ve sustained. While it’d be smart to take AC Milan on the moneyline with glorious odds if they were fully healthy, the team does have enough injuries that it makes the moneyline bet less attractive.

Taking Milan +0.5 goals still gives plus odds while also allowing for the chance of the teams splitting the points.

MORE: Updated Serie A standings

Chelsea vs. AC Milan prop: Over 2.5 goals

  • Prop kicker: Over 2.5 total goals (-125 on Caesars)

These two teams already struggle defensively, and thanks to injuries on both sides, goals could be flowing in this match.

For AC Milan, they saw right-back Davide Calabria and center-back Simon Kjaer both go down with long-term injuries against Empoli over the weekend, meaning Sergino Dest will likely get the start on the right flank in place of the team captain. The USMNT international Dest is an attacking-minded full-back that has improved defensively but still can struggle with getting caught high up the pitch. In pace of Kjaer, the young duo of Fikayo Tomori and Pierre Kalulu shouldn’t see too much of a drop-off, but losing the Danish international’s leadership will hurt.

On the Chelsea side, it will likely be Kepa Arrizabalaga in goal in place of Edouard Mendy who’s got a slight knee problem. Kepa has performed well of late, but he’s still the clear second-best goalkeeper in the Chelsea squad and is prone to the occasional high-profile mistake. The Blues are also still without N’Golo Kante which has been a significant problem to start the year, as Jorginho and Mateo Kovacic have been run ragged.

That adds to Chelsea’s already shaky defense, which has conceded 10 goals on 9.87 xG through eight Premier League matches, just the eighth-best back line in the English top flight.

For two teams that have lots of creative talent, the over should be doable here with the defensive frailties on both sides.

MORE: Everything you wanted to know about Chelsea boss Graham Potter

Chelsea vs. AC Milan prop flier: Rafael Leao assist

  • Prop flier: Rafael Leao to assist a goal (+450 on Caesars)

Once again, finding the best odds is key to discovering openings in this match. While Charles De Ketelaere is +320 to assist a goal, his creative partner Rafael Leao is all the way up at +450, laughable odds considering there are eight players above him in the list.

Leao has been spectacular up front this season, with his 2.02 xA (expected assists) good for 11th in Serie A, collecting that total in fewer minutes than all but four players in front of him. Additionally, his 3.53 xG (expected goals) total is more than anyone above him in the xA chart, meaning the Chelsea defense may be so focused on stopping Leao from scoring that he’ll be able to find teammates in open areas.

The 23-year-old picked up an assist against Dinamo Zagreb in Milan’s 3-1 victory a few weeks ago and could be primed for another Champions league assist at Stamford Bridge.



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