LONDON — A chastening night for Real Madrid coincided with a coming of age moment for Tottenham.
The European champions in three of the last four seasons were not just beaten in north London, but dismantled with ease by a Tottenham lineup lacking that kind of Champions League pedigree.
Such was Tottenham’s superiority, Madrid seemed fortunate to leave Wembley Stadium with only a 3-1 loss on Wednesday.
While Tottenham celebrated qualifying for the knockout phase for only the second time, the Champions League holders were reeling from their first group-stage loss in five years.
Coming directly after its Spanish league defence was hit by a surprise loss at Girona, the psychological impact will be even greater for Zinedine Zidane’s team.
"I am not worried," the Madrid coach said. "We played against a team who were better than us tonight and we have to accept it."
Madrid’s fragile defence was beaten too easily by Tottenham, a club that hasn’t won the English league since 1961 but has finished third and second in the Premier League in recent seasons. Dele Alli, suspended for the opening three games in Group H, made an explosive return to the Champions League with two goals.
Alli and Harry Kane then combined to set up Christian Eriksen in the 65th minute to build a commanding lead that ensured Cristiano Ronaldo’s strike in the 80th was a mere consolation for Madrid.
"It’s important we don’t just compete but we do win," Alli said. "We feel like we are a top side, and nights like this show we are."
The victory took Tottenham three points clear of Madrid at the top of the group, ensuring passage into the last 16 with two games to spare. Tottenham has only competed in the knockout phase once before — in the 2010-11 season when it was eliminated by Madrid in the quarterfinals.
Then, Madrid beat Tottenham 5-0 on aggregate, but the tables have turned. Last month, Tottenham secured a 1-1 draw in the Spanish capital and now it has beaten Madrid for the first time as Zidane endured one of the most painful games of his 22-month reign.
"After the loss in La Liga it’s always tough to recover from a morale point of view," Zidane said. "Now it’s going to be even more difficult, because that’s two losses in a row."
Tottenham’s victory came almost seven years since it beat another reigning European champion — Inter Milan — 3-1 in the group stage on Nov. 2, 2010 at White Hart Lane. Mauricio Pochettino’s team was dumped out in the group stage last season, but now appears far more adept among the continent’s elite.
"You have all seen today that Tottenham is a big team," Pochettino said. "We now belong not only among the best in England but in Europe. Results like these help people see where we are going."
And it was achieved with a core of inexpensive homegrown players, too. Three of them combined for the opener.
Harry Winks chipped a pass to Kieran Trippier, who squared the ball across the penalty area for Alli to squeeze into the net in the 27th.
This was a night of frustration for Ronaldo, summed up shortly after Alli’s goal when he hit the side netting and shot straight at goalkeeper Hugo Lloris. Ronaldo put his head in his hands.
It would get worse for Ronaldo.
The hosts sliced through the spine of the Madrid team in the 56th before Alli’s shot deflected off Sergio Ramos and wrong-footed goalkeeper Kiko Casilla to land in the net.
At the other end, Tottenham was adeptly neutralizing Madrid, and Ramos and Ronaldo were successfully crowded out when they were close to goal around the hour.
Another counterattack unsettled Madrid and ended with the third goal in the 65th. Alli released Kane, whose diagonal pass reached Eriksen. Luka Modric, in the Tottenham side that beat Inter Milan in 2010 before joining Madrid, was outmuscled by Eriksen and the ball was slotted into the net.
The only blots for Tottenham were a first-half hamstring injury for Toby Alderweireld, Alli missing out on a hat trick with an off-target header, and not keeping a clean sheet.
But a Tottenham side that has fallen short in the last two seasons when pursuing the Premier League title would not collapse against the European champions on a memorable night for a club that has won just one trophy this millennium, the League Cup.
"This means nothing if at the end of the season we haven’t won a trophy," Pochettino said.
Liverpool beats Maribor 3-0, tops Champions League group
LIVERPOOL, England — Liverpool cut loose after halftime to beat Maribor 3-0 and take a one-point lead in Group E of the Champions League on Wednesday.
Mohamed Salah and Emre Can scored either side of James Milner’s missed penalty before a late third by Daniel Sturridge, as Liverpool followed up its 7-0 win over the Slovenian team two weeks ago with another convincing victory at Anfield.
Liverpool can secure a top-two finish and a place in the knockout stage by beating Sevilla on Nov. 21 in the fifth round of games.
Sevilla beat Spartak Moscow 2-1 in the other group game Wednesday.
Liverpool peppered Maribor’s deep-lying defence with crosses in the first half but the visitors held firm, with goalkeeper Jasmin Handanovic tipping a deflected header from Roberto Firmino onto the bar.
The English team attacked with more midfield runners in the second half and finally broke through in the 49th minute when Trent Alexander-Arnold crossed for Salah to deftly flick a low volley past Handanovic.
Milner had been taken off penalty duties this season but, following misses from the spot by Roberto Firmino and Salah in the Premier League, the midfielder regained them when Firmino was tripped by Aleksander Rajcevic.
Handanovic guessed the correct way and tipped Milner’s shot onto the post.
The second goal arrived in the 64th when Can exchanged passes with Milner before sidefooting powerfully into the corner.
Sturridge came on as a 74th-minute substitute for Firmino and scored from close range in the 90th.
It mirrored Liverpool’s 3-0 win over Huddersfield in the Premier League on Saturday, with all of the goals coming in the second half then, too, after a lacklustre first half.
Porto beats Leipzig 3-1 to move second in group
PORTO, Portugal — Porto beat Leipzig 3-1 to reach second place in Group G of the Champions League on Wednesday.
Hector Herrera put the Portuguese hosts ahead early in the first half before Timo Werner came off the bench to equalize for Leipzig just after halftime.
Danilo broke the deadlock later in the second half and Maxi Pereira sealed Porto’s victory in injury time.
Porto reached six points from four matches, two points more than Leipzig but four fewer than Besiktas — held 1-1 by Monaco in Turkey in the group’s other game Wednesday. Last-place Monaco has two points.
Leipzig had beaten Porto 3-2 in Germany.
Porto next plays at Besiktas, while Leipzig is at Monaco.
Dortmund faces Champions League exit after draw with APOEL
DORTMUND, Germany — Borussia Dortmund and APOEL Nicosia played out a 1-1 draw on Wednesday which left both facing near-certain elimination from the Champions League.
Dortmund dominated but Raphael Guerreiro’s opener was cancelled out by Mickael Pote, who scored for APOEL in its second successive 1-1 draw with the Bundesliga side.
The draw left Dortmund and APOEL third and fourth respectively in Group H on two points apiece.
For either to qualify, they must now beat both Tottenham and Real Madrid in their final two group games. Group leader Tottenham defeated Real 3-1 in Wednesday’s other game in Group H to advance to the knockout stage.
Dortmund put its visitors from Cyprus under pressure from the start, and took the lead in the 29th minute when Shinji Kagawa’s pass opened up space behind the defence for Guerreiro to chip the goalkeeper.
Pote hit back for APOEL in the 51st. Carlao hooked in a low cross from the left and, though Pote almost lost the ball with his first touch, he recovered to turn and shoot past Dortmund keeper Roman Burki.
Dortmund piled the pressure on APOEL’s goal and frequently went close. APOEL’s players made desperate goalline clearances and were saved by the crossbar in the 77th when Pierre-Emerick Aubameyang’s header bounced off the woodwork and down.
Frequent penalty appeals from Dortmund’s players were turned down.
Marlos brace leads Shakhtar to 3-1 victory over Feyenoord
KHARKIV, Ukraine — Shakhtar Donetsk stayed on track to qualify for the Champions League knockout stage by beating Feyenoord 3-1 in Kharkiv on Wednesday, consigning the Rotterdam club to its fourth consecutive defeat in the competition this season.
The result left Shakhtar with nine points, three behind Group F leader Manchester City, which continued its rich scoring form to win 4-2 at Napoli.
As it did when it lost 2-1 to Shakhtar two weeks ago in Rotterdam, Feyenoord took an early lead and then squandered it.
Nicolai Jorgensen opened the scoring when he headed in Steven Berghuis’s cross in the 12th but Shakhtar equalized inside two minutes when Facundo Ferreyra saw his first shot blocked by Renato Tapia, but scored on the rebound.
Marlos gave Shakhtar the lead in the 17th and made it 3-1 with his second goal midway through the second half, cleverly dragging the ball past Tapia before chipping it over Brad Jones in the Feyenoord goal.
Feyenoord captain Karim El Ahmadi was left ruing missed chances.
"They had fewer chances than us, but scored three times," he told Dutch television.
Sevilla beats Spartak 2-1, moves to 2nd place in Group E
SEVILLE, Spain — Sevilla beat Spartak Moscow 2-1 to avenge its demoralizing loss to the Russian team two weeks ago and move to second place in Group E of the Champions League on Wednesday.
After being thrashed 5-1 by Spartak in Moscow, Sevilla rebounded with a solid performance at home, winning comfortably with goals by Clement Lenglet in the first half and Ever Banega in the second. Ze Luis scored late for Spartak.
The result left the Spanish side with seven points from four matches, one point behind leader Liverpool and two in front of Spartak.
Maribor, which lost 3-0 to Liverpool in England in the other group match, stayed with one point.
The result extended Sevilla’s unbeaten streak at home to 24 matches, with 17 wins and seven draws. Sevilla hasn’t lost at the Ramon Sanchez-Pizjuan Stadium since a 3-1 setback against Juventus in the Champions League almost a year ago.
Sevilla controlled the match from the start and opened the scoring with Lenglet’s close-range header in the 30th, and Banega added to the lead with a well-placed left-footed shot into the top corner in the 59th.
Ze Luis pulled Spartak closer with a goal in the 78th.
Sevilla next hosts Liverpool, while Spartak welcomes Maribor.
Spartak was not allowed to sell away tickets to its fans because of a flare thrown near the referee in the game at Maribor.
Besitkas closer to knockout stage after 1-1 draw with Monaco
ISTANBUL — Besikas moved a step closer to the knockout stages of the Champions League and pushed Monaco nearer the exit after the sides drew 1-1 in a closely-contested Group G game on Wednesday.
Striker Keita Balde missed a great chance to score the winner for Monaco deep into injury time, but his shot was easily gathered by home goalkeeper Fabri.
Ronny Lopes put Monaco ahead in first-half injury time with a fine strike from the edge of the penalty area.
But Cenk Tosun levelled from the penalty spot in the 54th minute after Brazilian defender Jorge brought down Ricardo Quaresma, sliding in naively just as the Portugal winger cut inside him.
Besiktas will go through if Liepzig wins away to Porto later in the group’s other game. Monaco reached the semifinals last season with some exhilarating attacking football, but has picked up only two points in four matches in this campaign and even reaching the Round of 16 is now a long shot.
Monaco lacked a cutting edge up front without top scorer Radamel Falcao, who sat out a second straight game with muscle fatigue.