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Gennaro Gattuso had been spoiling for a fight all night.

Peter Crouch was not built to react to the Milan midfielder's late lunges and provocation, Rafael van der Vaart and Steven Pienaar too amiable or astonished to respond to his antics, the officials seemingly unwilling to properly clamp down.

However, in the Tottenham technical area stood a square-jawed, shaven-headed Scot, eyes burning, dentures grinding. Joe Jordan had spent nearly half a century in football refusing to take a backward step and he was not about to start now.

Read more from BBC Sport's piece on the clash between Jordan and Gattuso here.

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By quirk of fate, it is one day short of being bang on 12 years since these two last met, also in a Champions League last-16 tie at the San Siro. And what a game that was!

It came in Tottenham's debut Champions League campaign, led by Harry Redknapp and during which Gareth Bale announced to Europe that he was destined for greatness by ripping Inter Milan to shreds.

On a wet and wild night, Peter Crouch's late goal gave Spurs a 1-0 win - one they would protect in a goalless second leg at White Hart Lane to progress to a last-eight tie with Real Madrid.

There was a lot more going on that night, though, including a couple of touchline clashes that are most people's overriding memory of the tie...

Simon Gleave
Head of sports analysis, Nielsen Gracenote

Tottenham Hotspur's tie against AC Milan is the most well matched of this week's four Champions League matches. However, Spurs are still reasonably strong favourites to progress to the quarter-finals with 58% chance of knocking Milan out. Tottenham are ranked 15th on our Euro Club Index, external while AC Milan are 21st. In the other match tonight, the second best team in Europe (Bayern Munich) faces Paris Saint-Germain, ranked 6th on our Euro Club Index. Bayern have a 65% chance of making it through to the last eight of the competition.

Katie Falkingham
BBC Sport

Liverpool want Uefa to "fully and transparently" fulfil recommendations made in an independent report on the events before last season's Champions League final in Paris.

Fans were penned in and teargassed outside Stade de France at the game against Real Madrid on 28 May 2022.

The report ruled Uefa bore "primary responsibility" for the chaotic scenes, adding it was "remarkable" no-one died.

Liverpool said action must be taken "to ensure there are no more near misses".

"It is remarkable that no-one lost their life."

That's the damning conclusion of an independent report into the chaos at last year's Champions League final between Liverpool and Real Madrid at Stade de France.

Fans have told of severe congestion, being attacked by locals and tear-gassed by police - one supporter called it a "carnival of horrors" which bore echoes of the 1989 Hillsborough disaster in which 97 Liverpool fans died.

The panel has concluded that European football governing body Uefa, as event owner, "bears primary responsibility for failures which almost led to disaster."

It also criticised the "reprehensible" attempt by authorities to incorrectly claim thousands of Liverpool fans without valid tickets caused the problems.

BBC Sport has picked out new detail and first-hand testimony from the report - including from fans who had also been at Hillsborough - outlining how events unfolded.

You can read that piece from BBC Sport's Frank Keogh & Katie Falkingham here.

Tottenham boss Antonio Conte: "If you want to win or achieve some targets and have a good position in the Champions League or in England in the Premier League, you have to be stable, and this stability is lacking this year.

"Sometimes players feel motivated, other times they feel so much under pressure that they can't perform.

"Maybe for a period, they have a good performance and then they collapse all of a sudden if they feel too much pressure.

"We are working on this; we want to make our players more resilient."

Pat Nevin says while Tottenham's midfield injuries are not ideal, Antonio Conte has options to find a solution against AC Milan.

Pierre-Emile Hojbjerg is suspended, while Rodrigo Bentancur is out for the season with a knee injury and Yves Bissouma needs an operation to repair a stress fracture to his left ankle.

Nevin told BBC Radio 5 Live's Football Daily: "If a player isn’t there you can’t moan or whinge about it, you’ve got to find an answer and there are some possible answers there.

"There is the possibility of Eric Dier going into the midfield. He’s played there very well, he’s comfortable in that position as well. Maybe his experience is really important to have at this point in time. But if you do that, you take him out of the back line and you don’t really want him out of there.

"Most Spurs fans will be really concerned. Bentancur is a big miss for them, but Hojbjerg has always been core to what they have done this season. Sometimes he does things that other players don’t enjoy doing and it’s not pleasant to watch.

"However he’s also got the creativity and he’s scored the odd goal as well. His physical presence on the pitch is massively missed for this one.

"What you want to do is make sure you are still in the tie by the time the second one comes around, but that is easier said than done. You are playing in one of the most iconic stadiums in the world against one of the biggest names in world football.

"But Milan have been a lot better than they are now and they have been going through a really difficult recent period."

Listen to UCL Away Days: Valentine’s in Milan on BBC Sounds

Tottenham come into this game off the back of a very chastening defeat, with Leicester taking them to the cleaners at the King Power Stadium.

Despite going ahead through Rodrigo Bentancur's first-half goal, Spurs never really looked in control and after Nampalys Mendy's thunderbolt equaliser hit the net they were comfortably second best.

It leaves Antonio Conte with yet more questions to answer in what has been an inconsistent season. They are still in the mix for the top four, with plenty of the season still to go. And tonight they have the chance to lay down a proper marker for qualification for the last eight of the Champions League. But with injuries mounting, the Tottenham players and fans need some cast-iron reasons to believe again.

Image source, BBC Sport

A one-off Football Daily podcast previewing Tottenham's Champions League last-16 first-leg tie against AC Milan is now live on BBC Sounds.

BBC Radio 5 Live’s senior football reporter Ian Dennis and former Chelsea winger Pat Nevin land in Milan before Tuesday's game at the San Siro, plus you will also hear from Spurs boss Antonio Conte.

Listen now on BBC Sounds

Everything Spurs in one place – bookmark the page or if you’re using the app hit the bell icon for club notifications

I feel like I need to offer a specific apology to all those partners of football supporters (especially of Tottenham) who are not fans themselves.

You may well find yourselves out on what you imagined was a romantic Valentine's Day date with your partner tonight. Fancy restaurant, good food, fine wine, maybe even some flowers on show. You'll look up from your plate and see your partner staring down at their lap, possibly with a look of tension or anguish on their face. If so, there is a chance it may be the words we're providing that they are reading on their phone.

Just know that they do love you. They just also love Spurs too. With a bit of luck, they'll win and you can have a lovely rest of the night.

Asmir Begovic
Everton goalkeeper on Final Score

Well I think that first and foremost it's a special night. To be playing at the San Siro, it has been a part of a few magical moments before in Spurs' history, so I think they're going into a lion's den. I think the San Siro will be on fire tonight.

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Be warned... if you're expecting to see a small, frail teenager get bullied in midfield for PSG tonight then think again. Warren Zaire-Emery may only be 16, but he's capable of mixing it with men twice his age.

He's primarily a defensive midfield with physical capabilities and stellar technique. He has represented France's youth teams from Under-16 to Under-19, and they know how to churn out serious young talent.

He has already made 11 appearances this campaign and has two goals to his name. In scoring against Montpellier at the start of February, he became the youngest goalscorer in PSG's history at 16 years and 330 days.

Pat Nevin
Former Scotland winger on BBC Radio 5 Live

Antonio Conte is not sure what Spurs are going to show up, so it's hard for the rest of us to figure it out. The hope is that what happened at the weekend was them taking their eye off the ball a little bit.

The capabilities of Spurs, when they play at their very best, they can take on anyone, they can score against anyone. They can score a load of goals against anyone.

I think, if this Spurs team turn up and play at their best or something approaching their best, over these two legs I think they'll go through, I would be that bold about it.

If they turn up like they did against Leicester, then this is going to be a long night.

If Spurs can keep it steady in midfield and get the ball to the quality they've got up front, they are better than Milan, it's as simple as that.

Ian Dennis
BBC Radio 5 Live senior football reporter

Milan are in the Champions League knockout stages after an absence of nine seasons so I can only imagine the atmosphere will be one to savour.

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Seeing Tottenham in top spot in Group D tells only a part of the story of how they reached the last 16 of this year's competition.

In a tough group also containing German side Eintracht Frankfurt, Portuguese team Sporting Lisbon and Marseille of France, Spurs headed into their final game - away at the last of those - knowing a draw would be enough to qualify.

They fell behind late in the first half, leaving them facing elimination to the Europa League, but a goal from Clement Lenglet put them on course and they then had to cling on before Pierre-Emile Hojbjerg's goal on the break, five minutes into added time, won them the group.

Image source, Getty Images

AC Milan had an inconsistent time of it in Group E, but ultimately had enough to qualify in second place. For all their flaws this campaign, Chelsea have performed well in Europe and it was they who took top spot.

Beaten twice by the Blues, Milan were unbeaten against the other two sides in the group - Austria's Red Bull Salzburg and Dinamo Zagreb from Croatia. They ended the group in fine form too, beating both of the aforementioned sides 4-0 en route to collecting 10 points overall.

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Paris Saint-Germain also cruised into the last 16, but they didn't have it as much their own way as Bayern.

Christophe Galtier's men also finished unbeaten in their group, but unfortunately for them found a Benfica side able to match them stride for stride.

Italian side Juventus and Israeli outfit Maccabi Haifa were both swept aside with ease, but there was nothing to separate the French and Portuguese sides, each of their two meetings ending 1-1. With an identical goals record of 16 scored and seven conceded, the group was ultimately decided on overall away goals scored, which Benfica had more of in large part down to the six they stuck past Maccabi in the final round of games.