Milan v Tottenham Prediction: Who Will Come Out on Top?

Milan v tottenham Milan v tottenham
TournamentChampions League 2023
TimetableWed 15th of February at 20:00
PredictionTottenham to win
Odds2.95 (Bet £‎100 and Receive £‎295 If Tottenham Win)
Tottenham to win
The best odds
Odds : 2.95
If Tottenham win, you will receive 2.95 x 100 = £295
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Odds : 2.55
If Tottenham win, you will receive 2.55 x 100 = £255

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There are just 16 of Europe's top teams that still have their dream of winning the 2023 Champions League intact, and soon this number will be cut down to just eight. Italy's AC Milan will battle it out with England's Tottenham Hotspur for a spot in the quarter-finals, and it is a clash that should have plenty of entertainment and drama. Who will win this first leg and give themselves the advantage for the second leg? Well, keep on reading and all will be revealed in this in-depth prediction.

Preview: The All-Important Date & Venue for Milan v Tottenham

The first leg of this Milan v Tottenham game will kick-off at the majestic San Siro Stadium on the 14th of February at 20:00 GMT. As this is just the first leg of this Round of 16 clash, both teams might be a little bit wary to start with as neither will want to make a mistake that could see them give their opponents an advantage heading into the second match. Despite the possibility of caution, we still think that this will be a great game to watch as there will be a number of quality players on display.

If you are in Milan on the 14th of February and do not have a ticket for this match, then head to a pub or bar and watch all of the action there. If Milan happen to go on to win, be sure to join in the post match celebrations with the AC Milan fans.

Milan v Tottenham History

Both Milan and Tottenham Hotspur are two teams that are well-known around the world, but when it comes to the number of trophies won, the Italian giants are way ahead of their English opponents. The Rossoneri have a total of 49 trophies in their cabinet, with their latest one being the Serie A title that they won during the 2021/22 season. Spurs, on the other hand, have won a total of 24 titles, but their last piece of silverware came back in 2008 when they beat Chelsea to win the League Cup.

So, what type of success have both teams had in the Champions League? Well, this is what we are going to take a look at now.

Milan Champions League History

AC Milan, who are currently coached by Stefano Pioli, have a very proud history in the Champions League. To date, they have won this competition no fewer than 7 times, which is a record that can only be bettered by Real Madrid, who have a total of 14 titles under their belt. The last time that they won the Champions League was in 2007 when they beat Liverpool 2-1 in the final courtesy of a brace from Filippo Inzaghi. This was seen as some sort of payback after the 2005 CL final, which saw them blow a 3-0 half-time lead to lose 3-2 on penalties.

From 2014 until 2021, Milan and their fans had to be content with playing in the UEFA Europa League, but they eventually managed to qualify for the 2021/22 edition. However, their time back in the big time did not go to plan, and they were eliminated in the Group Stage. To be fair to Milan, they had a really hard group that included Liverpool, Atletico Madrid, and Porto. They have already gone one better this time around, and they will be hoping that their 2022/23 Champions League journey does not end here.

All of the top football betting sites do not give AC Milan much of a chance of winning their 8th title, but they will still be eager to go as deep as they can because there is plenty of money riding on each match. For example, if Milan go on to win this Round of 16 clash against Spurs then they will pocket £9.1 million. This might not seem like much to a Premier League club, but it can make all the different to clubs from less financially awarding leagues such as the Serie A, Bundesliga, and La Liga.

Tottenham Hotspur Champions League History

Tottenham Hotspur, who are currently coached by Antonio Conte, have regularly qualified for the Champions League in recent seasons, but they are yet to win it. Only five English teams have won the Champions League to date which are Liverpool (6), Manchester United (3), Chelsea (2), Nottingham Forest (2), and Aston Villa (1). They made it to the final of the 2018/19 edition and had a chance to join this club, but they seemed to get stage fright and ended up losing 2-0 to Liverpool at the Metropolitano Stadium in Madrid. Apart from this final appearance, the furthest they have ever been in this competition is the Quarter-Final stage which they reached during the 2011/11 season.

In all honesty, we do not see them making it to the final again, let alone winning it, but Conte and his men will be quietly confident about being able to overturn Milan and make it through to the last eight.

Milan v Tottenham Head-to-Head

When you are thinking about placing bets on any football match, it is important to take some time to look at the previous results between the two sides. Why is this the case? Well, it will give you an idea as to who has been more successful down the years, and this can end up having a big impact on what happens when the two teams line up against each other again. In sport, it is not unusual for one team to have a bit of a psychological edge over another team, and you should not underestimate the power that it can have.

With this in mind, below you can find a table that shows you the Milan vs Tottenham head-to-head record:

5th April 1972Tottenham Hotspur vs AC Milan2-1UEFA Cup
19th April 1972AC Milan vs Tottenham Hotspur1-1UEFA Cup
15th February 2011AC Milan vs Tottenham Hotspur0-1UEFA Champions League
9th March 2011Tottenham Hotspur vs AC Milan0-0UEFA Champions League

As can be seen from the above head-to-head table, these two teams have not met that often over the years, with their last meeting coming 12 years ago in 2011. However, when they do meet, it seems to be a close match, and we think that this game will not be an exception to this. If you opt to bet on this match, then have a look at some of these top Champions League betting offers.

Milan v Tottenham Highlights: Path to the Round of 16

Another thing that you should take a look at before you go ahead and place any wagers on a big Champions League match is the path that each team had to make it through in order to qualify for this specific round. Obviously, since there is a random draw, one team might have had to navigate a much harder route than their opponents. If this was the case and they still ended up performing better, then keep this in mind before you go ahead and slap down a wager.

When you are betting using your hard-earned cash, you should never rush into things because this is how you end up losing more bets. Now, while there is absolutely no guarantee that your bet will be a winner if you make sure to take your time, there is no doubt that doing plenty of research will improve your chances of placing a successful wager.

Milan's Route to the Round of 16

Milan were drawn into a group alongside Chelsea, Red Bull Salzburg, and Dinamo Zagreb, so it was not one of the hardest groups, in all honesty. From the six matches that they played, the Rossoneri won three, drew one, and lost two - this meant that they finished second in the group with 10 points, while Chelsea topped the group with 13 points. They had a couple of disappointing results such as a 3-0 and 2-0 defeat to Chelsea, which meant that they had to settle for second place and a draw against a team that finished in first place.

To be honest, they will be happy with a tie against Tottenham Hotspur since they could have faced the likes of Bayern Munich, Real Madrid, Benfica, or Manchester City. No disrespect to Spurs, but these four teams are a much harder prospect when it comes to qualifying for the quarter-finals.

Tottenham's Route to the Round of 16

Tottenham were drawn in a group with Eintracht Frankfurt, Sporting CP, and Marseille, and it was probably the most exciting group in terms of drama. Entering the final round of matches, all four teams could still qualify for the Round of 16, and with just a minute or so remaining in the Marseille vs Tottenham match, it looked like Spurs were going to have to settle for second place with Eintracht Frankfurt taking the coveted top spot. However, Marseille, going for a win, left themselves open at the back, and Hojberg slammed the ball home to send Tottenham top of the group. This broke Marseille's hearts because it meant that they finished bottom of the group and missed out on a spot in the UEFA Europa League by a solitary point.

From their six matches, Tottenham won three matches, drew two, and lost one to end up with 11 points and a +2 goal difference. Some impressive results for Spurs included a 3-2 home win against Eintracht Frankfurt and a 2-0 home win against Marseille. Their only defeat of the Group Stage was a disappointing 2-0 defeat away to Sporting CP - It had looked like the match was going to finish in a 0-0 draw, but Paulinho and Arthur both scored in injury time to win the match for their side.

Milan v Tottenham Odds

As we mentioned earlier, the top Europa League betting sites are not giving these two teams much hope of going on to win the 2023 Champions League. However, obviously, you can bet on the winner of individual matches such as Milan vs Tottenham. In the following table, you can find some of the best odds available at the top bookmakers for each team to go on and win this first leg and take an advantage into the second leg.

Milan to Win2.482.502.452.502.50
Tottenham Hotspur to Win2.952.902.882.552.55

So, as can be seem from Milan vs Tottenham odds in the table above, the top sportsbooks available to UK football bettors are expecting a pretty close match between these two sides.

Milan vs Tottenham Betting Tips

You can decide to put your hard-earned money on the winner of this first leg if you so wish, but there are plenty of other markets on offer that you can bet on should you decide against betting on the winner of this match. Below you can find some Milan vs Tottenham tips that you should keep in mind when you are thinking about betting on something in this match.

Both teams to score: There is plenty of attacking talent on display for both of these teams in the shape of Harry Kane, Son Heung-min, Dejan Kulusevski, Olivier Giroud, and Rafael Leao. To add to this, there are chinks in both teams' defensive line, with both struggling for clean sheets as of late. Therefore, we definitely think that both teams will be able to find the back of the net in this game.

Over 2.5 goals to be scored: With the aforementioned attacking talent and defensive frailties, we think that there is a very good chance that there will be at least three goals scored in this match. There is a very good chance, in our opinion, that this match will finish with a 2-1 scoreline.

Harry Kane to score: If you are the type of punter that likes to bet on a player to score, then we recommend that you think about putting your money on Kane to score. Kane has been a goal machine for both club and country, scoring 200 goals in 301 appearances for Spurs and 53 goals in 80 appearances for England. Kane scores goals for fun against some of the best defenders in the world, so he will definitely relish taking on a leaky Milan defence.

Theo Hernandez to be booked: If you are the type of football bettor that enjoys betting on a player to be booked because you like the higher odds that are usually on offer, then one player you might want to think about putting your money on is Hernandez. The Frenchman is great at bombing forward, but this means that he sometimes leaves himself open at the back. Therefore, it is not unusual for him to have to put in a last-ditch tackle or commit a professional foul in order to stop his team from conceding on the counter. Also, he is not shy when it comes to talking back to the referee if he thinks a decision has gone against him or his team. Thus, he is no stranger to picking up a booking.

If you have a unique bet that you want to place but you cannot see any odds for it at the bookmaker that you have signed up with, then you can think about making use of the request a bet feature. All that you have to do is contact your sportsbook, tell them the type of bet that you want to make, and then they will offer you odds that they think are fair. Then it is entirely up to you as to whether you accept them or not.

Milan v Tottenham Live Stream

You will not find any live streams for this Milan v Tottenham game at the sportsbook that you have opened an account with since sports betting sites do not own the broadcasting rights to show their customers live matches from huge tournaments like the Champions League. TV channels fork out a lot of money in order to buy the rights for these big football games, so bookies will obviously not have the permission to stream them to their customers for free. If you would like to watch this match live from the United Kingdom, then you can watch it on BT Sport Ultimate and BT Sport 1.

Our Final Prediction

The top sportsbooks reckon that this will be a close game between two evenly matched teams, and we happen to agree. Some predictors would opt to sit on the fence and predict a draw, but we actually think that there will be a winner. We feel that Tottenham will get a very important away win mostly due to the fact that they have a better attack than AC Milan. The Rossoneri have been leaking goals lately, and they are going to be coming up against an attack that can score goals for fun on their day. We would be really surprised if there were not any goals in this match, and we feel that Spurs will come out on top in the end.

Our match prediction: Tottenham to win.

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Tottenham to win