Milan vs Tottenham UEFA Champions League Prediction with Odds, Betting Tips and Free Bet Offers

Milan vs Tottenham Prediction UEFA Champions League banner Milan vs Tottenham Prediction UEFA Champions League banner
TournamentUEFA Champions League
TimetableTuesday 14th of February at 21:00 CET
PredictionAC Milan to Win!
OddsMilan to Win @ 2.11
BookmakerPalmslots Sport
AC Milan to Win!
The best odds
Palm​slots Sport
Odds : 2.11
Bet €100 and win €211 if AC Milan win.
Odds : 2.00
Bet €100 and win €200 if AC Milan win.

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Odds : 2.10
Bet €100 and win €210 if AC Milan win.
Milan vs Tottenham Hotspurs UEFA Champions League 2023 Milan vs Tottenham Hotspurs UEFA Champions League 2023

On Tuesday, 14th February, the UEFA Champions League betting returns after its usual winter hiatus, as the tournaments’ knockout phase commences and the remaining 16 sides look to further their European adventures.

One of the first matches will see Serie A giants AC Milan entertain EPL side Tottenham, with the first leg of their round of 16 clash taking place at the iconic San Siro stadium.

This is one of the more evenly matched second-round encounters, and both sides will be confident of beating the other over the two-legged tie. But will seven-time winners Milan take a conclusive step towards their first quarterfinal since the 2011/12 season, or can Antonio Conte’s lead his charges into the last eight for only the second time in his career? Let’s find out!

Update: Go read our 2nd Leg Tottenham vs Milan prediction and betting guide.

💯 Milan vs Tottenham Champions League Odds

Before I take a closer look at these two sides and preview the first-leg clash at the San Siro, I’m going to check out the latest Milan vs Tottenham Champions League odds. Here’s a glimpse at the latest match betting odds that have been provided by the recommended betting sites at Betinireland.

AC Milan to Win2.
Spurs to Win3.303.453.503.303.603.503.50

⚽ Milan vs Tottenham Odds: Both Teams to Score

If you like to engage in match betting markets but can’t pick a winner here, you may want to consider backing both sides to score (or not). Here are the very latest odds in relation to this particular market.


🥅 Milan vs Tottenham Odds: Over/Under 2.5 Goals

As we have delved in our football betting guide, you can also bet on whether there will be over or under 2.5 goals scored in the game. This is a popular, even-money wager that can offer genuine value, especially if you have knowledge of the competing sides and their respective abilities. Here’s the latest odds.

Over 2.5 Goals1.731.731.831.751.911.801.80
Under 2.5 Goals1.831.911.951.951.881.911.91

🏅 AC Milan Champions League Round of 16 Leg 1 Preview

Milan have endured a difficult season in defence of their 2021/22 Scudetto, recently slipping 12 points behind Serie A leaders and into fourth place following a 4-0 thumping at the hands of Lazio.

Domestically, Milan are now winless in their last six matches dating back to January 4th, with this sequence including a 1-0 Coppa Italia defeat to Torino and a 3-0 loss to bitter rivals Inter in the Supercoppa Italiana. Most recently, they slumped to an embarrassing 5-2 home defeat to lowly Sassuluo, falling further behind league leaders Napoli in the process. As a result, Milan conceded at least four goals in consecutive matches for the first time in their history, as the side’s defensive issues became increasingly apparent.

While this is a troubling run of form, the Rossoneri have at least fared a little better in this season’s Champions League, qualifying for the round of 16 from a difficult group including Chelsea and an energetic RB Salzburg side. Sure, the group stage campaign included two comprehensive defeats against the Blues, but they’ll be optimistic that they can be more competitive in the tie against their EPL rivals from the capital.

Milan will be without talismanic striker Zlatan Ibrahimovic for the first leg, while right-back Alessandro Florenzi is also expected to miss out with a hamstring strain. Influential centre-half Fikayo Tomori continues to struggle with a hip injury too (he limped off in the defeat against Lazio). However, first-choice goalkeeper Mike Maignan may have recovered from a calf complaint in time for the first leg.

📰 Latest AC Milan Champions League News

⚡ Tottenham Champions League Round of 16 Leg 1 Preview

Like Milan, Spurs have also endured a slightly underwhelming 2022/23 campaign so far, with their Premier League form including seven wins and seven defeats since the 6-2 thrashing of Leicester City on September 17th, 2022.

More recently, they’ve incurred three EPL defeats in five matches, including a tame 2-0 defeat to bitter North London rivals Arsenal and a loss by the same score at home against Aston Villa. As a result, Spurs are now placed fifth in the Premier League and three points off the top four, having played a game more than nearest rivals Manchester United.

However, Spurs have at least sought some solace in their Champions League campaign, qualifying top of a group that included Eintracht Frankfurt, Sporting Lisbon and Marseille. This was one of the tightest and most keenly contested groups in the tournament, with Spurs only confirming their last 16 place following a last-gasp, 2-1 win at Marseille on matchday six.

Spurs will be without their influential defensive midfielder Pierre-Emile Højbjerg for the first leg against Milan, with the Dane collecting his third booking of the tournament in the aforementioned clash with Marseille (he also scored the winner at the Stade Vélodrome). However, Brazilian forward is expected to be fit for the match at the San Siro, despite his recent struggles with a hamstring injury.

📰 Latest Tottenham Hotspurs Champions League News

🆚 AC Milan vs Spurs Key Matchups

Teams have to work incredibly hard to be successful at the highest level, where matches are often decided by individual duals and battles that are largely physical in nature. But what are the key matchups in the Milan vs Tottenham clash, and how will they impact the outcome of the game?

1️⃣ Simon Kjær vs Harry Kane

English centre-back Tomori injured his hip in the chastening 4-0 loss against Lazio, with the 33-year-old Danish veteran Simon Kjær replacing him before half-time. He’s also expected to line up against Spurs if Tomori fails to recover in time, meaning that they’ll have to do battle with Spurs’ talismanic forward Harry Kane.

Despite Spurs’ obvious lack of creativity and attacking fluency, Kane remains as ruthless as ever in attack. He has also evolved into an effective creative outlet himself, regularly dropping deep to receive possession and creating space for players like Son Heung-min and Dejan Kulusevski to run into.

So, while Kane won’t trouble the space in behind Kjær or target his relative lack of pace, the Dane will have to decide whether to stay tight to Kane and follow the striker or leave him for a midfielder to pick up when he drifts deeper.

Regardless, Kjær will need to stay alert and communicate with his teammates at all times, while Milan will need to remain compact if they’re to prevent Kane from impacting the game.

2️⃣ Rafael Leão vs Emerson Royal

Antonio Conte continues to deploy a rigid 3-4-3 formation at Spurs, although this is likely to manifest as a more defensive-oriented 5-4-1 at the San Siro. However, there will be space for Milan to exploit in the wide areas, with Portuguese starlet Rafael Leão expected to pose a significant threat from the left flank.

Certainly, Leão’s will look to use his pace and dribbling skills to trouble Spurs wing-back Emerson Royal, while also looking to run in behind his opponent when the ball is switched from the opposite flank.

While Royal is quick enough to keep pace with Leão, the jury is out when it comes to the Brazilian’s broader defensive and positioning skills, while it may be hard for him to get forward and offer a viable attacking outlet on the right-hand side.

This could prove to be a key battle, especially if Milan are to sustain their attacks and pen Spurs back in their own half.

3️⃣ Sandro Tonali vs Yves Bissouma

Spurs’ formation often leaves them outnumbered in central midfield, and this will certainly be the case at the San Siro if Milan deploys Sandro Tonali, Ismaël Bennacer and former Manchester City starlet Brahim Díaz from the start.

This could be an even bigger issue in the absence of Hojberg, as while likely replacement Yves Bissouma is a capable player, he lacks the experience and positional awareness of the experienced Danish international.

Certainly, the intelligent Tonali and Diaz will look to press Bissouma and create overloads in the midfield, making it much easier for Milan to retain possession and preventing Spurs from countering regularly and at pace.

Tonali in particular will be key if Milan are to control the game through measured and attack-minded possession, but he’ll have to win his individual duel with Bissouma to have the desired impact.

📈 Milan vs Tottenham Head-to-Head Statistics

Milan and Spurs have only ever played each other twice in their illustrious histories, although both matches came during a round of 16 Champions League clash in the 2010/11 season.

The first match took place at the old White Hart Lane, with a game and dogged Spurs side eking out a hard-fought 0-0 draw against a more seasoned Milan outfit. Dutch legend Clarence Seedorf was included in the Rossoneri’s starting 11, for example, while Ibrahimovic and precocious Brazilian Alexandre Pato led the line in London.

While Milan were favourites to win the return leg, Spurs once again defied their more illustrious opponents with a dogged and organized display, before Peter Crouch stunned the home side with a winner 10 minutes from time.

Spurs were subsequently eliminated by Real Madrid in the quarterfinals, but they’ll be looking to overcome Milan once again and help head coach Antonio Conte to reach the UCL’s last eight for only the second ever time as a manager.

🏆 Milan vs Tottenham Prediction – Who Will Win?

Not only are neither of these sides in particularly good form, but they will also be missing one or more key players when the first leg commences at the San Siro.

This, coupled with the two-legged nature of the tie, could see a tentative and scrappy game in Italy, during which the home side may look to dominate possession and play on the front foot while Spurs defend deeper and try to hit on the break.

However, this could prove to be a dangerous tactic for Spurs, with Milan boasting technically excellent players in the middle of the park and wingers who will look to hold their width and penetrate in behind their opposing wing backs.

Because of this (and the enforced absence of the dogged Hojberg), I’m predicting a narrow win for Milan here, although their defensive absentees and subsequent frailties mean that Spurs will remain dangerous on the counterattack throughout.

⚽ My Milan vs Tottenham Prediction: AC Milan 2 Tottenham 1 🏆

🔍 Milan vs Tottenham Betting Tips

There are multiple Milan vs Tottenham betting markets that you can target before and during the first leg, although some of these offer considerably more value than others.

Here are my top three bets below, along with the relevant Milan vs Tottenham odds and the latest, real-time pricing.

1️⃣ Milan to Win at 2.11 With PalmSlots Sports

Milan’s status of favourites is reinforced by all of our recommended sportsbooks, and while their clash with Spurs should be relatively even and keenly contested, there’s definitely value in backing the Rossoneri to win the first leg.

You can get on this at a current market-high price of 2.11 at PalmSlots Sports, and I’d recommend placing this wager sooner rather than later and before the odds shorten as the game draws closer.

If you want to strategically increase your risk and potential returns, you could consider backing Milan to win and both sides to score at the San Siro. Spurs certainly retain a potent and clinical threat on the break, and you can bet on this outcome at a price of 4.40 with William Hill.

Get Milan @ 2.11 with PalmSlots Sports

2️⃣ Both Sides to Score at 1.73 With Unibet

Both sides certainly possess attacking quality, with Milan boasting several highly creative midfielders and outstanding dribblers like Rafael Leão. The experienced Olivier Giroud is also expected to lead the line, with France’s record goalscorer having netted 10 goals in 26 matches in all competitions in 2022/23.

As for Spurs, they retain considerable pace and movement on the counterattack, while Kane, Son and Kulusevski are more than capable of exploiting the space in behind Milan’s relatively high defensive line.

At the same time, Milan could be without two of their most important defensive players in the first leg, while the side’s recent defensive issues will give Spurs hope of creating chances and scoring.

So, although I’m backing Milan to win, there’s also considerable value in simply backing both sides to score. You can wager on this at a price of 1.73 with Unibet, although once again, the odds are liable to change prior to kick-off.

3️⃣ Over 2.5 Goals at 1.91 With Unibet

Instinctively, you may be inclined to bet on their being under 2.5 goals scored in this game, especially given Spurs’ defensive discipline and the enforced absence of Zlatan Ibrahimovic from the Milan side.

However, there are plenty of goals and creativity throughout the Milan side, while the likes of Kane and Son boast the pedigree and movement to punish the Serie A giants when they overcommit in attack.

Despite their defensive orientation, Spurs have only failed to score in four of their 30 games in all competitions this season, so they remain a significant threat even if they’re starved of possession.

So, I’m expecting there to be more than 2.5 goals scored in the first leg of this match, with this outcome priced at a competitive 1.91 by Unibet.

🎁 Champions League Free Bet Offers to use on AC Milan vs Tottenham

However you choose to wager on the clash between Milan and Tottenham, you can unlock additional value through our sportsbooks’ generous range of welcome bonuses and free bet offers.

I’ve listed some of the best offers below while taking a closer look at the three most generous promotions currently available.

1️⃣ Luckster – 100% Deposit Match up to €100 (No Wagering):

Currently, Luckster is running a generous and wagering-free welcome bonus to its new players, who can receive a 100% deposit match up to the value of €100. This could unlock a number of free bets on the Champions League, whether you want to bet on Milan vs Tottenham or any other round-of-16 clash. The minimum qualifying odds in play here are 2.00, while any deposits made through PayPal, Neteller or Skrill won’t be eligible to receive the bonus.

2️⃣ PalmSlots Sports - 100% Deposit Match up to €100:

While PalmSlots Sports is also offering new customers a generous, 100% deposit match up to the value of €100, this will be subject to wagering requirements of 16x the total bonus funds received. This dictates the total amount that you’ll have to play through before you’re able to complete a withdrawal, while any free Champions League bets that you place on the AC Milan vs Tottenham game must have minimum odds of 1.80.

3️⃣ Ladbrokes – Wager €5 and receive €20 in Free Bets:

Dominant UK and Ireland brand Ladbrokes have been running this particular welcome bonus for some time, with new customers eligible to receive four, €5 free bets (worth €20) when they make a qualifying wager of €5 or more. You can use your qualifying or free bets on the UCL clash between Milan and Tottenham, so long as your selections boast odds of 1.50 or over. You’ll have seven days to deploy the free bets after placing the qualifying wager.

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❓ Frequently Asked Questions About Milan vs Tottenham Prediction

So, there you have it; my detailed AC Milan vs Tottenham Champions League prediction and expert take on the latest odds. Before I go, however, I thought I’d answer some of your most frequently asked questions about the game, so that you can make informed decisions when placing your wagers!

1️⃣ AC Milan vs Tottenham Champions League Leg 1 – Who Will Win?

I’ve tipped Milan to win the first leg against Spurs at the San Siro, although the Rossineri’s defensive frailties will make the hosts vulnerable to Tottenham’s rapid and trademarks counter attacks. Because of this, I also think that both sides are likely to score in Milan, in what should be a close and keenly contested game.

2️⃣ What’s the best price for Milan to beat Tottenham?

If you agree with me and want to back Milan to beat Tottenham, I’d urge you to get on this at 2.11 with PalmSlots Sports. This is the best straight match betting price in the current market, and you should probably wager sooner rather than later before the odds start to shorten as the game draws closer.

3️⃣ Where Can I Watch Milan vs Tottenham?

Other than attending the iconic San Siro itself, you can watch the first leg between Milan and Tottenham on February 14th live on BT Sport. The game kicks off at 20:00 GMT, while you may also want to check to see if the action is being livestreamed by your sportsbook of choice (which is ideal if you intend to place in-play bets).

4️⃣ Is the Draw a Good Option?

While I’ve tipped Milan to beat Tottenham, there’s also some value to be found in betting on the first leg ending in a draw. After all, the game will see two evenly matched and relatively consistent sides do battle, while the draw can be backed at a market high price of 3,50 with TonyBet Sports and Luckster.

AC Milan to Win!

✒️ Lewis Humphries – Football Betting Expert and Tipster

Lewis Humphries is an experienced football writer and tipster from the UK. He writes regularly about the Champions League, Premier League, Serie A and other competitions, regularly delivering expert match predictions and betting insights. He also successfully predicted the winner of the 2022 FIFA World Cup, while accurately forecastingthe outcome of several group stage and knockout games.

Lewis doesn't just stick to sports; you can also find plenty of online casino gaming content. He's reviewed some of the world's leading casino platforms, while creating blog posts and landing page content for various sports betting brands.His content has also been featured on a number of different sites, including Life Hack, Investopedia, Yahoo Finance and Business Insider. He also pens regular sports features for sites including 90 Minutes, Think Football Ideas and Sportsblog.

Want to read more UEFA Champions League predictions written by our talented sports expert Lewis? Find them here!