A win would clinch a spot in the knockout stages of the Champions League, but, as they often do, Spurs refused to do things the easy way.
Tottenham went behind 2-0 initially, but they recovered to beat Olympiacos 4-2 to secure the second spot in Group B. Harry Kane bagged a brace while Dele Alli and Serge Aurier each added a goal to lead Spurs to a victory that seemed in doubt in the initial stages of the action.
Jose Mourinho made it two wins in two matches as manager of Spurs, with this being his first victory at the Tottenham Hotspur Stadium.
Mourinho’s second lineup for Spurs was quite similar to his first one. The only change was Danny Rose coming into the side for the injured Ben Davies.
In hindsight, it was not the right lineup. Eric Dier and Harry Winks struggled just as they have whenever they’ve been called upon this season.
The evidence of this was apparent right away. It was a disastrous start for Spurs.
There was a warning sign of the trouble to come when Paulo Gazzaniga had to bat away a deflected effort from the visitors, but he couldn’t stop the next shot that came his way.
Youssef El Arabi cut inside and fired a laser into the side netting. The chance was created because of a poor clearance from Rose, and an even worse attempt at a tackle from Winks.
Winks’ brutal season for Tottenham continued, as did the rough start for Spurs.
Olympiacos almost had a second when Daniel Podence capitalized on a giveaway from Winks to breakaway towards goal. Luckily for Spurs, Davinson Sanchez had the speed and strength to get back and stop him.
But Spurs couldn’t survive the Winks mistake that came a few minutes later.
The 23-year-old was weak at the near post on a corner kick, which allowed the delivery to be flicked on by Podence. That flick was swept home by Ruben Semedo from right in front of the goal.
It was such a gross showing to start the half that Mourinho went to his bench in just the 29th minute. Dier, again, looked slow, so Christian Eriksen came on in his place to try and bring the home side back into the game.
Things were still frustrating offensively until Tottenham were gifted a goal right before the break. Yassine Meriah whiffed on a low cross that he should have easily cleared, and Dele was there to tap in.
The lead had been cut in two, but it was still a disappointing first half performance from Spurs on a night when a win would clinch progression to the next round.
There was newfound desperation from Mourinho’s squad in the second half.
Sanchez almost equalized immediately when he made contact with a free kick in the box, but his header was all wrong and went over the bar.
The Colombian should have scored, but Kane struck a few minutes later to rectify his mistake. Aurier was smart to take a throw early, and his toss set Lucas Moura into space down the right. Moura’s cross was perfect for Kane, and the England international did the rest.
Afterwards, Mourinho hugged the ball boy who had gotten the ball into Aurier’s hands so quickly.
But the Lilywhites weren’t happy with just a point. They increased the intensity of their press as Olympiacos seemed to tire following their Herculean effort in the first half.
It was Aurier who struck the decisive blow on 73 minutes. Dele did so well to keep the possession alive, and then a header from Son Heung-Min came over into the Ivorian’s path. Aurier produced a sensational volley as he struck the ball perfectly to swerve it into the side netting.
Tottenham Hotspur Stadium erupted, but Spurs weren’t done yet.
Kane added another just a few minutes later off a free kick. Eriksen delivered a great ball, and all it took was a glancing header from Tottenham’s talisman to secure his brace.
The two tallies for Kane made him the fastest player to reach 20 goals in the history of the Champions League. It only took him 24 games.
The last of the two essentially ended the match. The Greeks were spent and put up little resistance as the home side saw out the game professionally.
The final whistle sounded and Spurs were into the knockout stages of the Champions League.
Elsewhere, Bayern Munich smacked Red Star Belgrade 6-0. This means that matchday six’s contest between Bayern and Spurs means nothing, as the Germans have clinched the top spot in their group.
Up next for Mourinho and company: Bournemouth, who will travel to North London on Saturday for a crucial clash in the Premier League.