Powder-puff Tottenham's season plunges into black hole as Milan end their Euro hopes

Champions League Round of 16

Tottenham (0) 0

AC Milan (0) 0

Aggregate: 0-1

Tottenham’s unravelling season has all but hit its nadir in the space of a couple of weeks as another insipid performance put paid to their last remaining shot at silverware.

This was a game they should have lost. Never mind the scoreline. Milan controlled proceedings more or less from start to finish and missed chances to put the game to bed.

But they were never seriously troubled at the back and the night was summed up 12 minutes from time when the eternally reckless Cristian Romero picked up a second yellow to leave his team-mates outnumbered for the final knockings as the Italians passed the ball around at will.

There is still a notional fourth place to fight for in the remaining 12 Premier League games, but this dismally low ceiling of ambition will test everyone’s loyalty and patience now.

The future of Harry Kane and Antonio Conte – culpable for adopting such a cautious approach – will surely now come into question more than ever.

Defeat at Sheffield United in the FA Cup and to Wolves in the league meant they went into this game on a low and they could not find a way to lift themselves back to the necessary levels for such a tie.

If Tottenham’s entire season rested on this fixture, you wouldn’t have known it from the way they approached the first half.

Passive from the start, and failing to press, they allowed Milan to get their feet firmly under the table and the Rossoneri very quickly looked as comfortable as could be.

It was a stark contrast to Chelsea’s front-foot approach against Dortmund the night before and baffling with a 1-0 deficit to make up.

Milan needed unsettling but instead they were handed a welcome mat.

The Italians were more than happy as the first 45 minutes played out with no shots on target for either side and a combined XG of 0.2. For those familiar with those sorts of details, it was basically an indicator that goals were out of the question.

That is very much in keeping with this strange, strange season for Spurs, who have made scoring first-half goals something of a taboo. Then again, second half goals have recently been a problem too.

And as if to underline what a dreadful half it had been, both Romero (naturally) and Clement Lenglet got themselves booked to trigger suspensions for the next round – which admittedly did not look a likely prospect even at that stage.

Spurs had to improve after the break. They looked more purposeful, even if it needed Fraser Forster’s legs to be in good working order to deny Brahim Diaz an opener.

Pedro Porro came on for Ivan Perisic to provide more width down the right and was soon getting involved as Spurs tried to raise their staccato tempo.

The South Stand began to find its voice. Even more so when a barreling run by Pierre-Emile Hojbjerg ended with a rising near-post drive which was tipped over by Mike Maignan in goal.

But the most dangerous player on the pitch was arguably Rafael Leao, whose nimble footwork inside the box presented Olivier Giroud with a half-chance that Forster stopped and there were late chances which should have been put away by a dominant Sandro Tonali and by sub Divock Origi, who struck a post with the goal gaping.

A Kane header did test Maignan from a set-piece but a goal would not have been deserved. Nor is it likely it would have been a springboard for the hosts prevail in extra time.

Yet underpinning the final moments were the memory of another brainless and thuggish act from World Cup winner Romero.

He is proving a liability. There is no discipline from him. No weighing up of when to leap in and when to hold back. It’s all about maiming anyone in his way. It’s no way to base your team’s strategy.

It has to be said that this was a game low on quality. The last time Milan visited – another goalless draw 12 years ago – Luka Modric was in the ranks for Spurs. TV presenter Jermaine Jenas and renowned golfer Gareth Bale were on the subs bench.

The Rossoneri’s team included Zlatan Ibrahimovic, Chelsea’s Thiago Silva and the great Clarence Seedorf.

This time out, big personalities were glaringly absent.

It was only the sixth competitive meeting between the clubs and Spurs have still never lost at home to Italy’s most successful European Cup entrants. But this draw felt very much like a defeat.

Spurs: (3-4-3) Forster – Romero, Lenglet, Davies – Emerson Royal (Richarlison 70), Skipp, Hojbjerg, Perisic (Porro 53) – Kulusevski (Sanchez 83), Kane, Son.

Milan: (4-3-3) Maignan – Thiaw, Tomori, Kalulu, T Hernandez – Junior Messias (Saelemaekers 56), Krunic, Tonali – Brahim Diaz (Bennacer 81), Giroud (Origi 81), Rafael Leao (Rebic 89)

Attendance: 61,602