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Tue 14 February 2023, 09:00|Tottenham Hotspur

On Tuesday evening, we take on AC Milan in the opening leg of our Champions League round of 16 tie (kick-off 8pm UK).

Here’s all of the game’s key points of note…

1 - Conte’s San Siro return

The San Siro is a stadium Antonio Conte knows well. The home of our opponents AC Milan, the historic and legendary stadium is also home to their city rivals Internazionale; a side Antonio once managed.

At the helm for Inter between 2019 and 2021, our Italian Head Coach led the Nerazzurri to the Scudetto in 2021 and so has, naturally, not just managed at the San Siro, but enjoyed many a fine moment there. Having also coached Juventus between 2010 and 2014, Antonio has overseen 59 games in total at the Guiseppe Meazza stadium, winning 39 matches and losing just eight.

2 - Conte vs AC

And Milan are a side Antonio has seemingly relished facing across the years as he boasts quite the record against them. In his last nine meetings with AC, his sides have won eight times (L1) and in each of his last away trips there, his side have kept a clean sheet.

SPURSPLAY - Antonio previews Milan clash

3 - The Italian job

When it comes to us facing Italian sides, we have an entirely even record. Having played 18 competitive matches against teams from Italy in our history, we have won six, drawn six and lost six.

4 - Versus Milan

Despite that even record versus Italians sides, against Milan, we remain unbeaten in all of our meetings. Having faced the Rossoneri four times to date, we have won twice and drawn twice. On all four occasions, our meetings have come across two legs, with both of those ties seeing us win the first leg before drawing the second. That includes our most recent clash with them in 2011.

5 - Our last meeting

We last encountered AC Milan in a competitive match back in the spring of 2011. Almost 12 years to the day – and at the same stage of the competition as we are now - we travelled to the San Siro in our first ever Champions League knockout game and we enjoyed quite the evening.

That night, Peter Crouch put the finishing touches to an explosive Aaron Lennon breakaway in the final 10 minutes to earn us a memorable 1-0 win in Milan. We then battled to secure a draw 0-0 with the Rossoneri in north London which secured us a place in the competition's quarter-finals.

Michael Dawson on that debut Champions League campaign and that night in Milan

6 - Our round of 16 record

While we of course enjoyed the highs of that debut outing in the Champions League knockout stages, it is fair to say in our campaigns since that we have endured mixed results.

Having qualified for the round of 16 five times to date, of the four ties to have been played, we have progressed from two (Milan 2010/11 and Borussia Dortmund 2018/19) and exited from two (Juventus 2017/18 and RB Leipzig 2019/20).

Highlights: Spurs 3-0 Borussia Dortmund | 2018/19

7 - European away days

And, while we have had a mixed bag of results in the round of 16, it is also worth noting our mixed results away in Europe in general. While we might have won on our last trip to the continent (a 2-1 triumph over Marseille), prior to that, we had won just one of our last 10 such matches (D3 L6).

Highlights | Marseille 1-2 Spurs | 2022/23

8 - Milan in the Champions League

This, of course, is a competition that Milan have quite the pedigree in, having lifted the European Cup on seven occasions however, over recent years, they have struggled to reach those heights.

With the last of those titles having come in 2007, they have since found difficulty in progressing through the knockout stages. In their seven subsequent campaigns in the competition, they have managed to progress through the group stage each time however on just one occasion have they got past the round of 16 – that was in the 2011/12 season as they reached the quarter-finals.

9 - Our strong European run

We are currently enjoying one of of our best-ever Champions League runs. Heading into tonight's game, we are currently unbeaten in our last four matches (W2 D2) - we last enjoyed a better run in the 2018/19 season as we went on a run of seven unbeaten as part of our journey to the final. We are also unbeaten in our last two away matches, drawing 0-0 with Eintracht Frankfurt in October before defeating Marseille 2-1 in November. We have never won back-to-back away games in the competition though so could make history tonight.

10 - Perisic's assist record

Ivan Perisic has been a key contributor in our progress in the Champions League this term. A veteran of the competition having almost made half a century of appearances in it (46), five of them have come this season in our colours and, in those matches, he has provided three assists. That return matches his best-ever return in a campaign in the competition having also provided three in Bayern Munich's run to the crown in 2020. As he returns to his former home of the San Siro tonight (he represented Inter Milan between 2015 and 2022), he'll be looking to go one further.