AC Milan vs. Chelsea best bets, expert prediction, betting odds, and picks for Champions League rematch

It’s rematch week in the Champions League group stage, as all teams that played last week will now meet again at the opponent’s home venue.

That means Chelsea, who secured a resounding 3-0 victory at Stamford Bridge last Wednesday, will travel to the San Siro to meet AC Milan in an attempt to earn superiority in Group E. Both teams are level on four points in the standings, one behind RB Salzburg’s five.

The Blues secured victory over AC Milan at home last week on goals from Wesley Fofana, Reece James, and Pierre-Emerick Aubameyang. The 3-0 victory over Wolves over the weekend saw another three goals scored by a trio of forwards, all of whom are fighting for playing time. Milan, meanwhile, stomped Juventus further down the Serie A table (2-0), meaning both sides enter this match on the heels of a resounding league victory.

A victory for either club would go a long way towards securing a knockout stage spot, with significant competition presented by RB Salzburg and Dinamo Zagreb. Yet a draw would put both sides in a precarious position with only two matches remaining.

MORE: How Chelsea cruised past AC Milan in their opening matchup

AC Milan vs. Chelsea betting odds

Chelsea are understandably considered favorites after last week’s result, but Milan are given a significant boost thanks to the friendly confines of the San Siro, where they are nearly perfect this season (five wins and one loss in six matches overall).

The Blues, who were minus-odds underdogs last time around, now see their odds to win climb into plus territory.

The betting market expects both teams to find the back of the net, but the under is slightly favored, meaning bookmakers are quite unsure how this match will play out.

AC Milan vs. Chelsea recent history

• AC Milan vs. Chelsea all-time: Chelsea 2 wins, AC Milan 1 win, 3 draws

Prior to last week’s meeting, these two teams had only faced off five times in history, across two total matchups, with the points split evenly. Last week changed that as Chelsea took over the all-time series lead.

Most recently, the two sides had matched up in the 1999/00 Champions League group stage. Ultimately though, AC Milan would finish bottom of that group with six points, while Chelsea and Germany’s 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, 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.

AC Milan vs. Chelsea last 5 matches

AC Milan vs. Chelsea prediction

In last week’s betting preview, I predicted that AC Milan would be able to match a struggling Chelsea side at Stamford Bridge. That proved to be dead wrong, as AC Milan were putrid on both ends. The final three-goal margin still flattered Chelsea and their 1.14 xG, but they put together three “big chances” and took them all, while AC Milan pieced together a paltry 0.42 xG total on just four shots.

It will now be up to Stefano Pioli to re-energize a quality attacking Milan side at home to save their Champions League lives. Unfortunately, the injury list is still lengthy, with starters Zlatan Ibrahimovic, Simon Kjaer, Mike Maignan, Davide Calabria, and Alexis Saelemaekers all out. That leaves the attacking load squarely on the shoulders of Rafael Leao and Olivier Giroud, whom Chelsea kept under lock and key last week.

Yet over the weekend, the Italian side were given hope as they pummeled Juventus at home with an attacking onslaught in which Brahim Diaz starred in the 2-0 win. Milan have proven far better at home, and with that, they can likely manage a draw, but securing all three points will remain a tall order.

• Moneyline lean: Draw
• Against the spread lean: AC Milan +0.5
• Scoreline prediction: AC Milan 1-1 Chelsea

AC Milan vs. Chelsea best bets, expert prediction

AC Milan vs. Chelsea best bet

• Pick: Both Teams to Score — Yes (-130 on Caesars)

It’s really, really difficult to back AC Milan in this match after what we saw last week. Chelsea were far and away the deserved winners at Stamford Bridge, but Stefano Pioli is a savvy coach who can identify the necessary countermoves.

Against Juventus, he brought in Brahim Diaz to great effect, as the Spaniard provided a goal and was incisive in the final third. Diaz replaced Charles De Ketelaere in the central playmaker role behind Olivier Giroud, who has been ineffective in his last few matches after enjoying a three-game scoring streak.

Aside from a mid-September loss to Serie A leaders Napoli, AC Milan have been quite literally perfect at the San Siro this season, including wins over Inter and Juventus in league play plus a 3-1 Champions League victory over Dinamo Zagreb. It makes backing a potential draw entirely plausible, with both teams likely open to taking attacking risks given a point does little for either side.

AC Milan vs. Chelsea prop: Corners

• Prop: Chelsea to earn most corners (-105 on Caesars)

Chelsea’s first goal at Stamford Bridge last week was generated on a succession of three consecutive corners all met by Chelsea defender Thiago Silva. The final effort was eventually deposited on the rebound by Wesley Fofana.

Somehow, Chelsea managed just a single corner the rest of the match, and still managed to out-gain AC Milan on the whole, with four corners to Milan’s three.

With Chelsea using both an aerial and crossing superiority to great effect throughout the match (more on that shortly), it would be shocking if the players aren’t able to prompt more set-pieces on the road. Chelsea generate around 6.5 corners per match in Premier League play, and they should come out on top of an AC Milan team that averages 5.2 in the Serie A.

AC Milan vs. Chelsea prop flier: Aubameyang headed goal

• Prop flier: Pierre-Emerick Aubameyang to score a header (+1000)

So how did Chelsea beat AC Milan last week? Simple: Graham Potter asked both wing-backs Reece James and Ben Chilwell and attacking midfielder Mason Mount to beat opponents on the dribble and then wreak havoc in the middle with crosses.

It worked to perfection. Those three players combined to complete six of eight attempted take-ons and delivered eight accurate crosses on 10 attempts. Those numbers are both utterly spectacular, and it resulted in a goal and assist from James, who stood out above the rest.

There’s no reason for Potter to change his attacking approach, as it created both first-leg goals, including Aubameyang’s goal (Chelsea’s second) on a cross from James. While it wasn’t a header, it feels like he could be teed up for one in this second leg.

Aubameyang isn’t a volume shooter with his head, but he buries the chances he gets. Over the last two league seasons for Aubameyang with Arsenal and Barcelona, the Gabon international has scored four headers on 17 shots, collecting 0.196 xG per shot, a very healthy total.

And while we’re at it, AC Milan’s aerial abilities are poor. The Italian side has won just 39 percent of their aerial duels in their three Champions League matches, and 53 percent in league play, which isn’t great for a top side that gets half their league games against less competitive clubs.

Pierre Kalulu especially struggles, at under 50 percent in league play. Between Chelsea’s proficiency crossing the ball, Aubameyang’s proficiency with his head, and AC Milan’s inability in the air, this could be a winning formula for this flier bet.