AC MILAN and Tottenham Hotspur contest the first leg of their Champions League round of 16 tie at the San Siro on Tuesday night.
The Rossoneri – who are the second-most successful team in the history of the competition, – reached knock-out stage for the first time in nine years after navigating their way through Group E where they were housed alongside section winners Chelsea, as well as Salzburg and Dinamo Zagreb
Closer to home, things have not been quite as simple for Stefano Pioli's side as their Serie A title defence is already in tatters, despite Friday night's 1-0 win over Torino.
That much-needed victory snapped a seven-game winless streak for Milan so they will be hoping that could be the catalyst they need to get them moving back in the right direction.
As for Tottenham, their season has been plagued by inconsistency, as further typified by the 4-1 pasting they suffered at Leicester in the Premier League on Saturday, on an afternoon where one of my King Power picks copped.
Former Inter Milan boss Antonio Conte is now tasked with lifting the spirits in the Spurs dressing room ahead of Tuesday's trip to the San Siro.
Outright Betting
Despite already losing to London-based opposition at home in this season's Champions League, AC Milan enter this first leg tie as marginal 8/5 (William Hill) favourites.
Tottenham, who have triumphed in just one of their last five Champions League away matches, arrive in Italy as 9/5 (Bet 365) outsiders while an all square affair can be backed at 11/5 (William Hill).
Betting Angles
It's difficult to have much faith in either team here but backing both teams to score looks like a worthy alternative at 7/9 with SBK.
While history would suggest that first leg ties have a tendency to be tight and cagey affairs, I'm prepared to go against the grain here given that neither defence is watertight and each side is capable in attack.
AC Milan's woes this season can be attributed to the fact they have filed just five Serie A clean sheets in 22 attempts so far, not to mention their backline was breached in four of their six Champions League group games.
What's more, both teams have obliged in a league-high 15 of Milan's 22 league games in Serie A this season, including eight of their 11 assignments at their San Siro home.
It's been a similar tale for Tottenham this term from a defensive standpoint as they have conceded 2+ goals in an alarming 13 of their 23 English top-flights outings to date, and they like their Italian hosts registered just two shutouts during pool phase.
With that in mind, coupled with the fact that BTTS has been a winning bet in each of Spurs' last three continental contests, siding with the same play on Tuesday night looks worth taking on at 7/9 (SBK).
I unsuccessfully backed Harry Kane to score at Leicester last time out but I make no apology for siding with a similar selection here in the To Score or Assist market at even-money (PaddyPower).
The England skipper has only scored once in this year's Champions League so far but he looks overpriced to have goal involvement here given how out-of-sorts AC Milan's rearguard has been in recent months.
This UEFA Champions League match between AC MIlan and Tottenham Hotspur will be played on Feb 14, 2023 and kick off at 20:00. Check below for our tipsters best AC MIlan vs Tottenham Hotspur prediction. You may also visit our dedicated betting previews section for the most up to date previews.
In December 2020 we sadly 
