Thursday, May 23, 2024

Prediction: AC Milan vs Tottenham

Verdict: Tottenham double chance

Best Odds: 6/11

Bookmaker: Unibet

Getting their Champions League knockout stage adventure underway on Tuesday night, Tottenham will make the trip to the San Siro when they meet AC Milan.

AC Milan

Starting with the hosts, while AC Milan might have managed to make a much-needed return to winning ways over the weekend, it doesn’t cover what has been a nightmare spell for the Italian heavyweights. Although Stefano Pioli’s side might have opened the 2022/23 campaign with their sights set on reclaiming their domestic crown, there appears to be a huge amount of pressure on the ex-Lazio boss. Despite being last seen a few days ago clinching a gritty 1-0 victory at home against Torino, that was the first win that AC have recorded from any of their previous eight matchups across all formats. With that run stemming all the way back to January 4th, Tuesday’s hosts have also shown some extended European issues on home soil. While Pioli’s men might have shocked many as they punched their knockout stage ticket prior to the World Cup break, it should be noted that the Rossoneri have won just a pair of their previous nine Champions League showdowns at the San Siro.

Team News

While goalkeeper Mike Maignan is inching closer to a return following a calf injury, the 27-year-old will not feature on Tuesday night. AC Milan have already confirmed that Ismael Bennacer will also miss out here.

Despite returning from a long-term lay-off, veteran striker Zlatan Ibrahimovic will likely have to settle for a spot on the bench in midweek.


As for the visitors, while it might have appeared that Tottenham had turned a real corner, there is no doubt that Spurs came crashing back down to earth over the weekend. Putting in a nightmare display and suffering a woeful collapse at the King Power, Antonio Conte’s side were eventually hit with a 4-1 drumming at the hands of Leicester. Watching their three-match winning run come to an abrupt end, the former Chelsea boss will be desperate for his side to make an immediate response on foreign soil. Knowing that they face a real uphill struggle if they’re to claim another essential top-four finish in 2023, Tottenham are seeking some much-needed stability. Although the Premier League outfit might have clawed their way to the knockout stage of this year’s tournament, Spurs have shown some continued Champions League issues outside of north London. Despite claiming that crucial 2-1 victory away at Marseille on November 1st, that is the only European away win that Tottenham have claimed from their last five attempts.

Team News

Tottenham will be hugely excited to welcome back defensive talisman Cristian Romero when they travel to Milan on Tuesday night. Fraser Forster should keep his spot between the sticks with Hugo Loris facing a lengthy spell on the sidelines.

Rodrigo Bentancur will miss the remainder of the season after picking up a knee injury away at Leicester last weekend.

Key Factors to Consider

    • This is the first time since 2011 that AC Milan and Tottenham have met in Champions League action.
    • AC Milan’s 1-0 win at home against Torino last weekend was the first victory they have collected from their previous eight attempts.
    • Likewise, Tuesday’s hosts have won just a pair of their last nine Champions League contests at the San Siro.
    • On a similar note, Tottenham have recorded just a single Champions League win outside of north London from their previous five attempts.
    • Each of Spurs’ final three group stage contests finished with both teams finding the net.


    Coming off the back of a woeful collapse at the King Power over the weekend, Spurs will be desperate to claim an immediate boost here. Although Conte’s side might be tipped as an underdog pick on Tuesday night, they should travel to the San Siro smelling the chance to spring an upset. While AC Milan might have claimed a much-needed 1-0 victory at home against Torino a few days ago, it doesn’t cover what has been a remarkable blip for the reigning Italian champions. Showing a string of issues since opening 2023, the midweek hosts have remarkably claimed just a single domestic win from their last nine straight appearances. Although we could have a cagey affair on our hands, we’re backing an away double chance here.

    Verdict: Tottenham double chance

    Best Odds: 6/11

    Bookmaker: Unibet


    Tom Dunstan

    Formerly of The Independent, Tom has spent the past six years as one of our senior writers and betting experts. Alongside working with numerous publications from across the globe, Tom also graduated from the University of Falmouth in 2014 with a Bachelor of Arts Degree in Digital Media.
    Spending almost the past decade working in countries such as Australia, New Zealand and Canada, he has also spent time featuring in sports radio. Tom can be followed on Instagram - @iamtomdunstan



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