For some reason, Tottenham Hotspur have become the kryptonite for Pep Guardiola’s Manchester City.

Their record since Spurs moved from Wembley back to the site of White Hart Lane has been abysmal, and it was a run which started less than a week after the Lilywhites returned home.

Tottenham Hotspur Stadium opened in April 2019 with Spurs beating Crystal Palace 2-0 in the Premier League. It featured fireworks, light shows and the Go Compare Man singing.

But the true ‘opening night’ came in their Champions League quarter-final against Man City. Here’s a look back at that fateful evening in N17.

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The first Champions League game in Tottenham in eight years saw Spurs beat tournament favourites Manchester City 1-0 in the first leg of their quarter-final.

Tottenham’s two-and-a-half season European odyssey at Wembley is over and after returning to their spiritual Haringey home last week with a win against Crystal Palace, they managed to conquer the English champions on a memorable night back in north London.

The visitors nearly found a half-sight of goal inside the opening minute when Raheem Sterling found David Silva waiting in the left channel, but his instinctive shot could only find the side-netting.

Spurs’ first chance came when Danny Rose’s ball into midfield was flicked on by Dele Alli and into the path of the marauding Mousso Sissoko. He returned the favour with a cross for Dele, only for his acrobatic effort cleared the crossbar.

With only 12 minutes on the clock, Man City were awarded a penalty. Sterling cut inside from the left and had a shot blocked by Rose, but after a lengthy VAR check, the left-back was judged to have made the intervention with his arm.

However, Sergio Aguero was unable to take advantage and his spot-kick was well-saved by Hugo Lloris, who dived down to his left to keep out the Argentine.

The hosts then quickly had two penalty appeals dismissed when Harry Kane was brought down by Nicolas Otamendi and then Dele by Aymeric Laporte as the pressure inside the new Tottenham Hotspur Stadium continued to ever increase.

Spurs went close midway through the first half when Dele cleverly pirouetted around Otamendi and found Christian Eriksen, whose first-time pass found Kane free inside the 18-yard-box. But the England captain seemingly didn’t realise just how much time he had and his quick snap-shot was pushed away by Ederson.

The first 45 ended with Tottenham in the ascendancy, but were let off the hook immediately after the break when ponderous defending allowed Sterling to gain a few yards of freedom in the box. Fortunately for the hosts, the resulting shot was calmly palmed away by Lloris.

At the other end, Son Heung-min came in from the right flank and curled a shot at goal from 25 yards, and Ederson was grateful that it just about landed on the other side of his post.

Kane dropped deep into midfield to rob Ilkay Gundogan of possession and played a neat one-two with Harry Winks to launch a quick counter attack, which ended with Son this time forcing Ederson into a low save.

The tie changed after 55 minutes when Fabian Delph clattered Kane’s ankle, and the Tottenham talisman immediately limped down the tunnel to the audible horror of the home crowd.

With under a quarter of an hour remaining, Man City had threatened to truly trouble Spurs from open play, and they were punished when Son broke the deadlock after 78 minutes. Eriksen’s clever ball between Delph and Laporte was met by the South Korean, whose skewed touch saw him scramble to keep it in play, eventually circling his way back round to the edge of the six-yard box and firing under Ederson.

Pep Guardiola threw on Kevin De Bruyne and Leroy Sane with six minutes of stoppage time looming, but Man City still failed to cause Tottenham any major problems and Mauricio Pochettino’s side will head to the Etihad Stadium with a precious one-goal lead and zero away goals conceded.

GK: Hugo Lloris – 8/10 – His penalty save changed the tie. Simple as.

RB: Kieran Trippier – 6/10 – Wasn’t his best day in terms of crossing but did just about enough to keep Sterling off the scoresheet.

CB: Toby Alderweireld – 7/10 – Sometimes guilty of cheaply giving the ball away but was largely solid defensively.

CB: Jan Vertonghen – 7/10 – Made a series of crucial interceptions when Man City tried to play through Spurs.

LB: Danny Rose – 7/10 – While at the time the handball call seemed harsh (particularly because not one Man City player appealed for it), the decision was probably correct. Nevertheless, Rose recovered well and kept Mahrez ever so quiet.

CM: Moussa Sissoko – 8/10 – Covered every blade of grass, sweeping up in midfield and carrying it up the pitch. Also provided extra protection for Trippier at right-back against Sterling.

CM: Harry Winks – 6/10 – Provided stability at the base of midfield both in and out of possession, though did sometimes get overrun by Man City’s press.

RM: Son Heung-min – 8/10 – The match-winner. Doubled up on Delph and tormented him down the right wing, spinning him inside-out.

AM: Dele Alli – 7/10 – Linked midfield and attack so well. Did well to win the ball high up the pitch and draw fouls, forcing Man City’s backline to reshuffle in accordance with his runs.

LM: Christian Eriksen – 8/10 – Spurs were able to play at varying tempos due to Eriksen’s ability to drop into midfield and spread passes at will.

CF: Harry Kane – 6/10 – Didn’t look too sharp, but that was largely because Man City players were essentially hitting him with a lead pipe all game until he eventually succumbed to his injuries.

Substitutes

Lucas Moura (58′ for Kane) – 6/10

Victor Wanyama (81′ for Winks) – N/A

Fernando Llorente (87′ for Dele) – N/A

Manager

Mauricio Pochettino – 8/10 – Could have easily set up to simply sit deep and counter Man City, but Spurs went toe-to-toe with them and were duly rewarded.

GK: Ederson – 6/10 – Bravely claimed several crosses and made a few decent saves, but there’ll be question marks over whether he could have done more to keep Son out.

RB: Kyle Walker – 5/10 – Roundly booed on his return to this part of north London. Spurs came inside to avoid his pacy defensive presence and he was essentially taken out of the game.

CB: Nicolas Otamendi – 4/10 – Played with over-the-top aggression and made it hard for Man City to pass out from the back with composure.

CB: Aymeric Laporte – 6/10 – The best of a rather bad bunch at the back for Man City.

LB: Fabian Delph – 2/10 – Clumsy, erratic, unfit, sent to the shops for Son’s winner. A terrible night.

DM: Fernandinho – 5/10 – Usually so cunning and clever, Fernandinho was second-best in a lot of his duels this time around.

CM: Ilkay Gundogan – 5/10 – Lost the ball a few times under pressure in the midfield battle. Just doesn’t provide the same threat as Kevin De Bruyne.

CM: David Silva – 6/10 – Wriggled his way into pockets of space but like Gundogan was unable to have the same impact on the game as De Bruyne from the off would have.

RW: Riyad Mahrez – 4/10 – Shrunk in his battle with Rose. Far too timid with the ball.

CF: Sergio Aguero – 3/10 – Missed a crucial penalty and was then swallowed up by Spurs’ two Belgians.

LW: Raheem Sterling – 6/10 – Man City’s most threatening outlet. Needed way more help out of his supporting cast.

Substitutes

Gabriel Jesus (71′ for Aguero) – 4/10

Kevin De Bruyne (89′ for Silva) – N/A

Leroy Sane (89′ for Mahrez) – N/A

Manager

Pep Guardiola – 3/10 – Made some strange team choices and reacted too late with his substitutions.

Player of the Match – Son Heung-min

Tottenham’s win was the result of a real team effort, and it would be very harsh to say that any given player didn’t have a good game. There were, however, a few standouts besides the obvious match-winner in Son Heung-min:

For whatever reason, Man City just can’t piece their Premier League dominance together in the Champions League.

A lot of the buildup to this game centred around their surprise exit to Liverpool at the quarter-final stage a year prior, falling three goals down early on in the first leg at Anfield.

Guardiola’s men had won their last three meetings with Spurs with relative ease, but played with an unusual trepidation this time around. The decisions not to play De Bruyne or Sane for longer also seemed odd.

Tottenham would ultimately advance to the semi-finals on away goals after Man City could only muster a 4-3 win at the Etihad Stadium a week later, with Sterling famously denied a tie-clinching goal deep into stoppage time by VAR.