Spurs secure a place in the knockout stages of the Europa League in Austria, despite a frustrating 3-3 draw against LASK Linz.
Jose Mourinho made three changes to the starting line-up that beat Ludogorets 4-0 a week prior.
Both strikers missed out through injury, and so Heung-Min Son started at the head of a front three, with Giovani Lo Celso and Pierre-Emile Hojbjerg starting instead of Harry Winks and Dele Alli.
LASK sat third in the group, needing a win against their opponents to have any chance of progressing into the next round.
As the game began, the home side played a very high intensity and closed down any opportunity that Spurs tried to create.
Just six minutes into the game, German striker Johannes Eggestein created some space on the edge of the Spurs box.
He thundered a right-footed curled shot towards the bottom corner, which beat Joe Hart in the goal, but unfortunately for the 22-year-old, the ball rattled off the post.
A poor start from the North London side.
Mourinho’s men continued to struggle throughout the first half and could not quite get a grip on the game.
In the 42nd minute, Matt Doherty surged forward down the right-hand side, but seemed to roll his ankle, which resulted in the Austrian side regaining possession.
A quick counter-attack into the huge gap that Doherty had left, pressured the Tottenham backline.
Winger Thomas Goiginger played the ball inside towards Peter Michorl, who unleashed a shot from around 25 yards out.
The ball nestled into the bottom right corner, beating Hart, and putting the home side into the lead.
Despite the setback, Spurs upped their game and a nice passage of play led to a penalty, just before halftime.
The penalty was conceded by Andres Andrade, with a hand ball from a Tanguy Ndombele shot.
Gareth Bale stepped up to take it, and confidently converted the ball into the bottom left corner.
A shaky first half for Tottenham, as LASK Linz dominated the majority of the half.
As the match resumed after the break, Dominik Thalhammer’s team continued their good football, with the Spurs players looking lacklustre.
However, against the run of play French midfielder Ndombele played a neat pass towards Son.
The Korean’s first pass to feet throughout the whole game put him one-on-one with the goalkeeper.
A chance that he relishes.
Son, without hesitation, drilled the ball past Alexander Schlager and into the bottom left corner, putting the away side into the lead.
As Mourinho looked to seal out the game, he made three defensive minded substitutions.
Moussa Sissoko replaced Lucas Moura, Eric Dier came on for Lo Celso and Serge Aurier was swapped for goalscorer Bale – who moments before squandered a two-on-one opportunity by passing the ball behind Son – which could have put the game to bed.
With six minutes to go, LASK attacked again, pushing for an equaliser.
A defence-splitting pass by Andrade created a chance for Werder Bremen loanee Eggestein.
His left-footed shot towards the near post caught the Tottenham keeper by surprise and was pushed into the back of the net.
The Englishman would have felt like he should have done better.
In spite of the goal conceded, Tottenham earned another chance.
Substitute Bergwijn received a lofted through ball over the defence of the Austrian team but was bundled over by Philipp Weisinger.
Another penalty was awarded to Spurs.
With no Gareth Bale on the pitch or Harry Kane, Dele stepped up to take it.
He calmly sent the goalkeeper the wrong way and dispatched the ball into the centre of the goal to put Spurs back into the lead in the 88th minute.
Four minutes were added on, with the Austrian Bundesliga team fighting for Europa League survival.
Reinhold Ranftl found Mamoudou Karamoko on the edge of the box, and the back three of Tottenham backed off, giving the Paris-born forward several yards of space.
The French striker curled a shot into the right corner, tying the score line in the 93rd minute.
A tough and frustrating evening for Tottenham nonetheless, who were favourites to win the game.
However, with Kane and Vinicius both side-lined, it was always going to be harder.
LASK Linz can be happy with their performance, as they put the Premier League leaders under pressure for the whole 90 minutes.
Unfortunately for the Austrian team, they would need 11 goals against Ludogorets, and Antwerp to beat Spurs in the final group stage fixture, for Round of 32 qualification.
In Tottenham Hotspur’s case, a huge game on Sunday against rivals Arsenal at the Tottenham Hotspur Stadium.
Although Harry Kane did not travel with his team-mates for the game this evening, Mourinho believes he will be fit for the North London Derby.
Overall, a bittersweet result for Jose Mourinho and his players, as it was a disappointing performance, but they are through to the knockout stages of the Europa League, continuing their good start to the season.