LONDON -- Tottenham Hotspur crashed out at the Champions League last-16 stage on Wednesday as defender Cristian Romero was sent off in a 0-0 draw with AC Milan.

Spurs needed to overturn a 1-0 first-leg deficit but lost by that score on aggregate after an insipid display at Tottenham Hotspur Stadium in which they mustered just two shots on target. Romero scythed down Rafael Leao to earn his first yellow card inside the opening 20 minutes and was sent off 12 minutes from the end for a reckless lunge on Theo Hernandez.

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In stoppage time, Harry Kane forced Milan goalkeeper Mike Maignan into his best save of the evening with a header from Son Heung-min's free kick, moments before substitute Divock Origi struck a post at the other end.

While Milan can celebrate reaching the last eight of Europe's premier club competition for the first time since 2011-12, Spurs are left to rue another trophyless season with a performance that will increase speculation over the future of head coach Antonio Conte.

Rapid reaction

1. Conte's future at a crossroads

Antonio Conte said he would "transmit my energy to the team" after returning to the Tottenham dugout following gallbladder surgery that kept him in Italy for most of February. Either he failed to do so in a disastrous fashion that should trigger a major rethink or he has nothing left to give. Spurs went out of the Champions League with barely a whimper here, a dour 0-0 draw which will only raise question marks over the future of their manager, who is out of contract at the end of the season.

Boos rang out at half-time and full-time. This was not a courageous, heroic exit from Europe but a meek surrender in which Conte's side looked a mixture of flat, fatigued and flawed. Spurs have often been passive in their matches before rousing themselves in the second half and while there was a modicum of improvement here, the collective lack of urgency throughout was nothing short of staggering given the stakes in play. Some frank conversations lie ahead.

There is a top-four race to concentrate on -- Spurs currently have a narrow advantage over Liverpool -- but this is a club at a crossroads. They need clarity soon to plan for the summer and beyond, with or without Conte. The fans passed their most pointed verdict yet. Some booed at half-time, more dissented as Conte changed Dejan Kulusevski for Davinson Sanchez late on but the majority made their anger known at the final whistle.

2. Tottenham's trophy drought goes on

The last time Tottenham won a trophy, George W. Bush was U.S. president, Lehman Brothers hadn't gone bust and the first iPhone had been on sale for less than a year. That League Cup victory in 2008 is a distant memory for so many Spurs supporters, who know their team plays in one of the world's best stadiums and trains at one of the finest centres around yet remains incapable of winning any silverware to show for it.

There was a degree of compromise in hiring Conte given Tottenham's desire to win with an expansive style the Italian is not famed for, but they felt it was a price worth paying given his undeniably impressive winning record. Yet he has been caught in the same cyclical failure that has enveloped Tottenham for 15 years; for all their progress under Mauricio Pochettino, despite possessing England captain Harry Kane as he chased down and surpassed Jimmy Greaves' all-time club record goal tally, they cannot achieve sport's ultimate aim of winning trophies.

There are wider issues which predate Conte, specifically a charge levelled by many at owners ENIC and chairman Daniel Levy that they have not invested sufficiently in the team to compete with their rivals. And that is a debate that will resurface in earnest now they have fallen short for another year.

3. Pioli achieves another Milan milestone

Stefano Pioli has struggled to recreate last season's consistency which saw AC Milan win their first Serie A title in 11 years. They currently sit fifth in the table, 18 points behind leaders Napoli and facing a scrap to qualify for next year's Champions League. However, he can now point to a first quarterfinal appearance in the competition since 2012, an achievement which should ease the pressure on the 57-year-old for the next few weeks at least.

Milan, seven-time European Cup winners, played with an authority that matches their history in this competition, rarely looking troubled aside from the final 10 minutes when the pace of the game became a little more frantic as Spurs, finally, took some risks. Last season Pioli's side finished bottom of a group containing Liverpool, Atletico Madrid and FC Porto. Now they can argue their case as one of the best eight teams in Europe.

Best and worst performers

BEST: Brahim Diaz, FW, AC Milan.
Gave Milan composure and authority in possession, almost scoring six minutes into the second half with a low shot well saved by Fraser Forster.

BEST: Rafael Leao, FW, AC Milan.
Not his most effective night in the final third but Spurs were terrified of his pace throughout.

BEST: Fikayo Tomori, DF, AC Milan.
Martialled the backline brilliantly, winning all three tackles and recovering possession eight times (only teammate Theo Hernandez managed more on either side).

WORST: Cristian Romero, DF, Tottenham.
Sent off for two wild challenges. Possibly the first player ever sent off while lying in the opponent's technical area.

WORST: Son Heung-Min, FW, Tottenham.
Had just 38 touches, the fewest of any Spurs outfield players to last 90 minutes. Registered one shot in a must-win game.

WORST: Ivan Perisic, MF, Tottenham.
Completed just nine of his 14 passes in an ineffectual display before being substituted on 53 minutes.

Highlights and notable moments

The game's best sequence came in the final throes of stoppage time with Harry Kane forcing an amazing save from AC Milan goalkeeper Mike Maignan, moments before Divock Origi's shot rattled the woodwork on the other end.

WHAT A SEQUENCE!

Tottenham almost score and Milan hit the post! ? pic.twitter.com/C5tamEnibc

— CBS Sports Golazo ⚽️ (@CBSSportsGolazo) March 8, 2023

After the match: What the managers and players said

Tottenham manager Antonio Conte on the game, to BT Sport: "That is the third game in a row that we were not able to score. I think the game was in the balance. I think we can do much better offensively. I speak about the whole team not only those who play in the front half. We can do much better.

Conte, on his future with the club: "I continue to work, I have a contract with Tottenham. I respect the contract. At the end of the season, assessments will be made with the club in the most serene way. ... Let's see how the season ends. Maybe they can send me away even earlier. Perhaps the expectations were higher and may be disappointed. What matters for a coach is trying to work and raise the bar. This year we are struggling to raise the bar."

Key stats (provided by ESPN Stats & Information research)

- With eight quarterfinals appearances in the Champions League, AC Milan are behind Juventus (12) for most by an Italian club.

- Cristian Romero has been sent off for the eighth time across his career (both club and country).

Up next

Tottenham Hotspur: Sitting in fourth place in the Premier League standings, they'll aim to stave off Liverpool and Newcastle United for the final Champions League spot for next season. Spurs take on Nottingham Forest on Saturday before Southampton on March 18.

AC Milan: Level on points with AS Roma for the fourth and final Champions League spot in the Serie A table, Milan will try to move up with two league matches next week -- Salernitana on March 13 and Udinese on March 18.