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In what will be a nostalgic night for both sets of supporters, the two European giants will clash for the first time since 2016 in a match of the ages.
The Reds won one of the most dramatic Champions League finals in the history of the tournament against Milan in 2005, coming back from three goals down to level the fixture before a famous penalty shootout.
Milan avenged that defeat in the final of 2007, and Wednesday should produce another exciting match with both teams unbeaten in the early stages of the season - but who will come out on top?
Ahead of the game, our tipster Robert Mann takes a look at some of the best bets from Liverpool vs AC Milan to get your teeth stuck into.
Liverpool are 4/11 to win, with AC Milan priced at 7/1 to come away with the victory. A draw is priced at 4/1.
Prediction: 2-1 (7/1)
Match Result and Both Teams To Score: Liverpool and Yes (15/8)
So far this season, the Reds have been brilliant, winning three of their first four matches and drawing with European champions Chelsea in the other.
With Liverpool scoring nine goals this season and Milan seven, we’re expecting this affair to be a high-scoring contest, however, the Reds' home advantage cannot be underestimated.
First Goalscorer: Mohamed Salah (5/2)
The Egyptian has scored three goals in four matches so far this season and we’re backing him to continue that stellar form tonight in Europe’s most competitive competition.
To Be Booked: Theo Hernandez (12/5)
The 23-year-old left-back faces a major test against the Liverpool forward line tonight and will, undoubtably, be prone to a foul or two against the likes of Salah and Sadio Mane’s ability to play anywhere across the front line.
Odds are correct at the time of publication and are, as always, subject to change.
Please gamble responsibly. For more information visit: https://www.begambleaware.org.
A European night in front of a full Anfield again...— Liverpool FC (@LFC) September 15, 2021
We've been waiting for this ❤️ pic.twitter.com/jplTOPncvU
Olivier Giroud should be cleared to take part in this fixture after recovering from coronavirus, and he should hope to reclaim place in Milan's attack over Zlatan Ibrahimovic - ruled out through injury.
We are finally #BackHome: let's relive some glorious memories with Paolo Maldini ❤️🖤— AC Milan (@acmilan) September 14, 2021
Le parole e i ricordi indelebili di Paolo Maldini: avviciniamoci così al tanto atteso ritorno in @ChampionsLeague ❤️🖤#LiverpoolMilan #UCL #SempreMilan pic.twitter.com/Z4L4etLn6H