AN all-Italian affair takes place in the Champions League on Wednesday night as AC Milan meet Napoli in the first leg of their quarter-final tie at the San Siro.
The Rossoneri – the second-most successful team in the history of the competition -progressed to the last-eight for the first time since 2012 after eliminating Tottenham in the round of 16.
While Stefano Pioli's side have easily surrendered their Serie A title this season, they will now be daring to dream of going all the way in this season's Champions League after being placed in the opposite half of the draw to the likes of Bayern Munich, Manchester City and Real Madrid.
Furthermore, Milan could have struck a psychological blow against Napoli as they dished out a 4-0 drubbing to the Italian league leaders just 10 days ahead of this showdown.
Having said that, Napoli have perhaps taken their foot off the pedal in Serie A given how far in front they are in, although they did return to winning ways with a 2-1 win at Leece last time out.
As for the Champions League, Luciano Spalletti's side reached the last-eight of Europe's premier club competition for the first time in their history by romping to a 5-0 aggregate win over Eintracht Frankfurt, with both of my bets landing in the second leg.
Outright Betting
Despite their aforementioned 4-0 win over Napoli earlier this month, AC Milan head into this first leg as 19/10 (Bet 365) outsiders while the draw has been chalked up at 9/4 (Boylesports).
Napoli turned AC Milan over at the San Siro back in September and they are 8/5 (UniBet) favourites to repeat the trick on Wednesday night.
Betting Angles
Napoli are worthy favourites here but with star striker Victor Osimhen an injury doubt for this first leg, I'm happy to instead side with the 17/20 (PaddyPower) price on Napoli in the Draw No Bet market.
This is a selection that will see our stake returned should this San Siro showdown end all square while a Napoli triumph would deliver a pay out.
With a first Scudeeto since the days of Diego Maradona all but sewn up, Napoli have afforded themselves the luxury of being able to put all of their eggs in a Champions League shaped basket between now and the end of the season.
While AC Milan will have home advantage and the confidence gained from their recent 4-0 rout of their fellow Italians, Napoli are a very different beast from all of the opposition they have faced in the Champions League this season so far.
Stefano Pioli's side were put to the sword home and away by Chelsea during the group stage and they really didn't really pull up any trees when squeezing past Spurs in the round of 16.
This is stark contrast to Napoli, who kick-started their Champions League campaign in spectacular fashion by scoring freely en-route to claiming top honours in group that included Liverpool and Ajax before eviscerating Europa League holders Eintracht Frankfurt over two legs
Therefore, with all things considered, I'm happy to back Napoli with a touch of insurance in the Draw No Bet market at 17/20 (PaddyPower) on Wednesday night.
Given that Khvicha Kvaratskhelia has been in supreme form this season, I'll also back the Napoli ace To Score Or Assist at 11/10 with PaddyPower.
The Georgian winger has either notched or provided a goal in 30 of his 32 appearances for Napoli this term, so the 11/10 (PaddyPower) on him to add to that tally here looks a lovely price.
This UEFA Champions League match between AC Milan and Napoli will be played on Apr 12, 2023 and kick off at 20:00. Check below for our tipsters best AC Milan vs Napoli prediction. You may also visit our dedicated betting previews section for the most up to date previews.
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