Tottenham vs Milan Prediction with Odds, Betting Tips and Free Bet Offers UEFA Champions League 2023

💯 Tottenham vs AC Milan Champions League Odds

Let’s start with a closer look at the latest Tottenham vs Milan betting odds, which are available across a broad range of markets and wager types. I’ll start with the latest match betting odds on the likely winner at the Tottenham Hotspur stadium.

Market
Tottenham to Win	1.90	1.91	1.98	1.91	1.95	1.91	2.00
Milan to Win	3.75	3.70	3.97	3.80	4.00	3.80	3.75
Draw	3.40	3.60	3.40	3.50	3.50	3.40	3.40

⚽ Tottenham vs AC Milan Odds: Both Teams to Score

Of course, there’s a huge range of match betting markets in play here, and you can also bet on both sides to score (or not) at the Tottenham Hotspur Stadium. But what are the latest Tottenham vs Milan odds in this respect?

Market
Yes	1.70	1.83	1.82	1.75	1.80	1.75	1.73
No	2.10	2.05	2.03	1.95	1.98	2.00	2.00

🥅 Tottenham vs AC Milan Odds: Over/Under 2.5 Goals

When wagering on the Tottenham Hotspur vs AC Milan second leg clash, you can also engage in totals betting. This includes over/under betting on the total number of goals scored that will be scored in the game, with this even money market usually offering excellent value by football betting sites if you’re a knowledgeable punter.

Market
Over 2.5 Goals	1.91	1.93	1.97	1.87	1.92	1.91	1.85
Under 2.5 Goals	1.89	1.83	1.85	1.83	1.85	1.83	1.85

⚡ Tottenham Hotspur Champions League Round of 16 Leg 2 Preview

As I’ve already touched on, Spurs have endured an indifferent run of form this season, which has seen them struggle to win consistently or play with any kind of sustained attacking fluency.

Since January 1st, Antonio Conte’s men have lost four of their eight Premier League games contested, including a harrowing 4-1 defeat at struggling Leicester City on February 11th. Although the side have also scraped unconvincing wins against Fulham and West Ham (and defeated defending champions Manchester City) during this run, they’ve only recently broken into the top four and remain seven points behind Manchester United in third place.

Even Champions League qualification for the round of 16 went to the wire, despite Spurs being drawn in a relatively favourable group with Eintracht Frankfurt, Sporting Lisbon and Marseille. This turned out to be an incredibly keenly contested group, with Spurs only confirming their second round place with a last-gasp, 2-1 win at Marseille on the final matchday.

The first leg in Milan was similarly disappointing, with Spurs struggling to break down their opponent’s defence on the counterattack. Milan retained a measure of control throughout, as their midfield largely dominated in the absence of influential Spurs’ pair Rodrigo Bentancur and Pierre-Emile Hojbjerg.

While Bentancur remains sidelined for the remainder of the season with a crucial ligament rupture, Hojbjerg will return to Spurs’ starting 11 after being suspended for the first leg. However, Tottenham will also be without number one keeper Hugo Lloris with a knee injury, while Ryan Sessegnon (hamstring) and Yves Bissouma (ankle) are expected to miss out.

📰 Latest Tottenham Hotspurs Champions League News

🏅 AC Milan Champions League Round of 16 Leg 2 Preview

Milan have undoubtedly endured a difficult season domestically, with their form in 2023 particularly worrying. Since the start of the New Year, they’ve played eight Serie A matches, winning just three of these and losing another three.

These defeats included a 4-0 thumping at Lazio and a 5-2 thrashing at home by Sassulo, while Milan also lost 1-0 to city rivals Inter to slip into fourth and 18 points behind an outstanding Napoli side at the top of the table. They also exited the Coppa Italia at the round of 16 stage, losing 1-0 at home to Torino at the San Siro.

However, Milan have at least won their last two Serie A games to return to some kind of form, while they showed enough quality and control during their first leg clash with Spurs to suggest that they’re more than capable of reaching the UCL quarterfinals.

In terms of team news, Milan will be boosted by the return of several players ahead of the second leg. Talismanic striker Zlatan Ibrahimovic is back in training, for example, while attacking right back Alessandro Florenzi has also recovered from a hamstring strain. First choice keeper Mike Maignan may also have recovered from a calf injury in time for the second leg, while defensive midfielder Ismael Bennacer will definitely be available for selection.

📰 Latest AC Milan Champions League News

🆚 Tottenham vs AC Milan Key Matchups

Regardless of which players take the field at the Tottenham Hotspur Stadium, the individual battles and duels that take place all over the pitch will have a key bearing on the final result. So, I’ve identified three duels that could be crucial during the second leg. These include:

1️⃣ Harry Kane vs Fikayo Tomori

Talented English centre back Fikayo Tomori should be fit to return to the Milan starting lineup in the second leg, which put him on a collision course with the outstanding Harry Kane.

While Kane is no longer as prolific as he once was (he has 19 goals from 33 matches so far this season and just one in seven UCL matches), he continues to play in a much deeper role for his side, making him increasingly illusive and difficult to mark as he looks to feed the forward runs of Son Heung-min, Dejan Kulusevski and Richarlison.

This will create a challenge for Tomori, who will have to decide whether to track Kane as he drops deeper or allow his midfielders to deny him space in the middle of the park.

If Tomori does decide to track Kane and stay tight to the striker, this could leave space for Spurs’ attacking runners to exploit in transition, so how Milan set up tactically will have a direct bearing on how they handle this threat.

2️⃣ Emerson Royal vs Rafael Leão

New signing Pedro Porro endured a horrific debut for Spurs at the King Power Stadium, as Leicester’s Harvey Barnes beat him at will on the Foxes’ left-hand side during Tottenham’s 4-1 defeat.

Emerson Royal subsequently returned to the starting 11 against West Ham, with the Brazilian getting on the scoresheet and playing with distinction and Spurs returned to the top four ahead of Newcastle.

He’s likely to start in the second leg against Milan too, where once again he will come up against the talented Portuguese forward Rafael Leão. This will be a huge challenge for Emerson, as despite his obvious pace and athleticism, he occasionally struggles positionally and may find it hard to cope with the Portuguese star’s dribbling ability.

This will be a key battle, especially with Spurs having to attack and overturn their first leg deficit and liable to leave space in behind their defensive line.

3️⃣ Pierre-Emile Hojbjerg vs Sandro Tonali

The return of Pierre-Emile Hojbjerg to Spurs’ midfield will be timely, as despite the endeavour and drive of Pape Matar Sarr and Oliver Skipp in the first leg, this youthful pair lacked the experience and technical ability to gain any measure of control at the San Siro.

They were also outnumbered centrally against Milan, and while this is a pitfall of Conte’s preferred 3-4-2-1 formation, Hojbjerg’s experience, class and positional sense will provide Spurs with a much more solid base to attack from at home.

Both he and his opposite number Sandro Tonali will look to dominate the middle of the park and possession at the Tottenham Hotspur Stadium, and Hojbjerg will need to call upon all of his nous and ability of Spurs are to sustain attacks and remain mindful of the threat on the break.

He’ll also need the support of his teammates, as his midfielder partner (most likely Skipp) and players like Kulusevski will have to work tirelessly to deny Tonali time and space on the ball throughout.

📈 Tottenham vs AC Milan Head-to-Head Statistics

The first leg clash at the San Siro was the third such match between Tottenham and AC Milan, with the latter claiming their maiden win over their Premier League rivals at the end of the 90 minutes.

The two previous clashes came during the 2010/11 UCL campaign, when Spurs and Milan were also drawn to play each other during the round of 16. A tense first leg took place at the old White Hart Lane, with a dogged and determined Spurs side earning a 0-0 draw against a more illustrious Milan outfit that featured the legendary Clarence Seedorf.

Incredibly, Zlatan Ibrahimovic also played in this game, but Milan struggled to score an all-important away goal in London. This led to a similarly taut and evenly contested second leg in the San Siro, with Spurs keeping an aggressive Milan side at bay before rangy striker Peter Crouch stunned the home crowd with an 80th-minute winner.

So, these sides have a completely even H2H record in European competition, winning one match apiece and drawing the other while scoring a single goal each.

🏆 Tottenham vs AC Milan Prediction – Who will Win?

Now it’s time for my Spurs vs AC Milan prediction, as both sides look to reach the UCL quarterfinals and re-establish themselves and serious players at Europe’s top table.

Neither side will arrive in London on a particularly impressive or consistent run of form, although both will be boosted by the return of key players to their starting lineup. The return of Hojbjerg for Spurs will be particularly important, with his experience and positional awareness crucial against a technically proficient side like Milan.

This is an incredibly even contest, with Milan’s technical superiority countered in part by Spurs’ greater firepower in the form of Kane, Son and Kulusevski. However, Spurs may have to advance out of their comfort zone and play a little more on the front foot given their first leg deficit, and this could afford Milan space and time to launch effective counterattacks.

Because of this (and the likely return of Tomori and Maignan to the Milan starting 11), I’m predicting a narrow win for Milan. The Rossoneri will subsequently advance to the quarterfinals, extending Antonio’s Conte’s miserable Champions League record in the process.

🔍 Tottenham vs AC Milan Betting Tips

If you want to bet on Tottenham vs Milan and its wide range of betting markets, you’ll need to identify value and ensure that your bankroll is deployed as effectively as possible. So, I’ve offered some key Tottenham vs Milan betting tips, so that you can hopefully make informed selections that optimise your chances of winning at Ireland's best betting sites.

1️⃣ Both Sides to Score at 1.82 with Luckster

The bookies appear to be somewhat split on whether both of these sides will score or not, as there isn’t a great deal between the published odds across both potential outcomes.

However, I believe that both sides are likely to score in London, especially with Tottenham required to chase the game and play in a way that doesn’t suit Antonio Conte’s philosophy. So, although I don’t expect Spurs to charge out of the blocks at the beginning of the second leg, they will have to take the initiative and look to score while keeping Milan out at the other end.

For their part, Milan have more than enough quality to counter effectively after winning possession, while the side will be much closer to full strength than it was during the first leg.

So, consider betting on both sides to score at 1.82 with Luckster, with this representing the best value odds in this market at the time of writing.

2️⃣ Over 2.5 Goals at 1.97 with Luckster

Luckster is also offering market leading odds of 1.97 that more than 2.5 goals will be scored in the second leg clash between Spurs and Milan, with the bookies considering this to be slightly less likely than the total goals tally being under 2.5.

Despite this, the nature of the tie and Milan’s first leg lead will create a more open game from the outset, especially as the removal of the away goals’ rule means that Spurs can focus on winning the game rather than being preoccupied with shutting out the Rossoneri at the other end.

So, it’s well worth betting on this market and getting on the price offered by Luckster, while this could make for a viable in-play wager if there’s an early goal in the game at the Tottenham Hotspur Stadium.

3️⃣ Milan to Win 2-1 at 13.00 with William Hill

While betting on the correct result in relation to any single game is risky, it may offer a little more value than usual when it comes to Tottenham vs AC Milan.

The reason for this is simple; as neither side is prolific, meaning that there’s unlikely to be a huge number of goals in the game.

Similarly, both sides can be relatively porous defensively, while the fact that Spurs will have to chase the game to some degree means that the second leg is unlikely to be particularly low scoring.

So, betting on a final score of 2-1 to Milan at odds of 13.00 with William Hill may potentially offer generous returns, even if you look to offset your increased risk by staking a relatively small amount!

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

Before you place your bets on the second leg clash between Tottenham and AC Milan, you may want to peruse some of the most generous free bets and welcome bonuses currently available.

I’ve listed 12 such free bet offers below, while highlighting three in particular that enable you to make the most of your bankroll and qualifying bets. These include:

1️⃣ Luckster – 100% Deposit Match up to €100:

Where else but to start with Luckster’s current welcome offer, which is available to all new Irish players and will match your first deposit by 100% up the value of €100. The wagering requirements in play here are competitive at nine-times the value of the bonus, while single bets must be placed on selections with odds of 2.00 or greater. In combination or system bets, all eligible selections must be played at minimum odds of 1.40, unless expressly stated or allowed with the permission of your chosen sportsbook.

2️⃣ William Hill – Bet €10 and get €40 in Free Bets:

New William Hill customers can also opt into a generous welcome offer, which comprises €40 in free bets when you place a qualifying wager of €10. The bonus can be further broken down into four separate €10 bets, each of which must be deployed on outcomes with odds of 1.50 or greater. William Hill is also home to a number of competitive Spurs vs Milan betting markets, so this is a good offer to cash in on when wagering on the second leg clash in London.

3️⃣ TonyBet Sports – 100% Deposit Match up to €50:

I also like the look of TonyBet Sports latest offer, which comprises a 100% deposit match up to the value of €50. To qualify, you’ll have to make an initial deposit of €10 into your new account, while entering the dedicated promo code TONY50 to opt in. The wagering requirements in play here are 10x the total bonus value, so you’ll have to play through a certain amount of money within 30 days before completing a withdrawal. All free bets must also be placed on outcomes with minimum odds of 1.65.

❓ Frequently Asked Questions About Tottenham vs AC Milan Prediction

So, there you have it; my detailed Tottenham vs AC Milan prediction, which includes a look at the latest odds and betting markets, up-to-date team news and some insightful wagering tips!

Before I go, however, I wanted to answer some of your most frequently asked questions about this second leg clash. So, let’s get into it!

✒️ 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.