There is a repeat of the 2005 and 2007 finals on Tuesday when AC Milan host Liverpool.
The pair endured contrasting returns from the international break - AC Milan winning for the first time in Serie A under new coach Paulo Fonseca, beating Venezia 4-0.
Meanwhile, Liverpool suffered their first defeat with Arne Slot at the helm, going down 1-0 at home to Nottingham Forest.
However, the Reds won home and away when the duo clashed in Group B of the 2021/22 UEFA Champions League and could open their new European campaign with a similar result.
Liverpool to win and both teams to score - 11/4
Both of those finals featured both teams scoring. Liverpool famously won on penalties in 2005, coming from 3-0 down to draw 3-3 and force extra-time before Milan deservedly triumphed 2-1 two years later.
Their two meetings in 2021/22 also featured goals for each side, Liverpool winning 3-2 at Anfield and then 2-1 at the San Siro.
Despite Saturday's setback, the Reds should not lose confidence and are further on in their development than Milan, with Slot taking over an already-improving team left to him by Jurgen Klopp.
In contrast, Fonseca has had to pick up the pieces after the Rossoneri's progress ground to a halt in the closing stages of Stefano Pioli's reign.
The Portuguese's stuttering start even saw the Milan fans unveil a banner declaring the Venezia game was his "last chance" before the Ultras would protest.
With Fonseca's team due to take on Inter in the first Derby della Madonnina on Sunday, it is a massive week for the 51-year-old and it looks set to get off to a losing start.
Mohamed Salah anytime goalscorer - 7/5
It could be Mohamed Salah's final season at Liverpool and lifting the UEFA Champions League Trophy for a second time in his career would mark a fitting end.
The Egyptian made a lively start to 2024/25, scoring in his team's first three Premier League games but looked sluggish on Saturday and understandably so, having represented his country against Cape Verde in Cairo before playing 75 minutes of their victory away in Botswana.
That's a lot of air miles, but a few days of relative rest will help him hit the ground running in Lombardy.
He scored home and away against AC Milan in 2021/22 and is certain to carry a threat at Stadio San Siro.
Ryan Gravenberch to be booked - 15/4
A player who appears to have benefited from Slot's appointment is Ryan Gravenberch, with the Dutch coach seemingly determined to repurpose his compatriot as a holding midfielder.
Gravenberch earned praise for his showings as a number six in Liverpool's three wins in August, but inevitably received criticism for his display against Forest.
However, the 22-year-old's energy means he is likely to keep his place at Stadio San Siro, although he is still learning his new role and has already received two bookings this season.
Staying goal-side of the ball has understandably proved tricky for a midfielder who has hitherto done his best work in the attacking third.
Milan are still adapting to Fonseca's tactics, but one thing they do have is exceptional mobility through their midfield trio of Ruben Loftus-Cheek, Youssouf Fofana and Tijjani Reijnders, meaning Gravenberch is likely to have to bring his man down at some stage of the game.
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AC Milan - 14/5
Draw - 14/5
Liverpool - 10/11
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This article was written by a partner sports writer via Spotlight Sports Group. All odds displayed on this page were correct at the time of writing and are subject to withdrawal or change at any time.
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