Fielding a much-changed side to the one that drew 1-1 with Newcastle, it was clear that Jose Mourinho had his eyes set on Thursday's Europa League playoff tie against Maccabi Haifa.
Timo Werner scored his first Chelsea goal to give Frank Lampard's side the lead in the 19th minute, with a sensational finish from the edge of the area.
Chelsea controlled possession and dominated territory for the rest of the first half. However, after the break, Tottenham put more pressure on the Chelsea goal, and got their reward late in the second half. After a bit of pinball inside the penalty area, Erik Lamela managed to slot an easy finish past debutant Edouard Mendy in the Chelsea goal.
Both sides didn't miss a penalty until the 10th of the shootout, which Mason Mount put wide, to send Tottenham through to the next round.
Here's how each player fared for both sides.
Tottenham Hotspur Player Ratings
Hugo Lloris - 6/10
He didn't have any chance to stop Werner's goal during regulation time. He did not save any penalties in the shootout either. However, he made a couple of very important stops in regulation time, especially one off Werner in the second half.
Japhet Tanganga - 4/10
Tanganga was rusty and made mistakes a little too frequently in this game. Considering he is just back from injury that is not a real cause of concern from Mourinho. Isolating this game alone though, Tanganga was chasing shadows, and committed a few mistakes that led to Chelsea chances.
Toby Alderweireld - 6/10
Playing in the middle of the back three, it was Alderweireld's job to ensure that the aerial threat of Olivier Giroud didn't hurt Spurs. The experienced Belgian was top notch with his defending in this game.
Eric Dier - 7/10
He had a slightly worry with a potential injury in the first half, but he managed to run that off. He was generally solid on the left side of the back three, and also scored his penalty in the shootout. However, this game will be remembered for Dier rushing off into the dressing room midway through the second half, to deal with a bodily function.
Serge Aurier - 5/10
He didn't really defend well in the first half, as Chilwell had the freedom of the whole flank to himself. Aurier was a lot better after the break though.
Gedson Fernandes - 6/10
Gedson didn't have real quality on the ball, but he harried Jorginho and the rest of the Chelsea midfielders into making mistakes. He was replaced by Pierre-Emile Hojbjerg in the second half.
Tanguy Ndombele - 7/10
His quality in possession was generally outstanding in this game. He was press-resistant, and helped Spurs get out of some tight spots.
Moussa Sissoko - 6/10
Lots of energy but little direction as he struggled to stem the tide of Chelsea's flowing football.
Sergio Reguilon - 6/10
He gave the ball away first, and then dived in unnecessarily on Azpilicueta in the build-up to Chelsea's goal. The blame for that falls squarely on him. But he redeemed himself by crossing the ball for Spurs' equaliser.
Steven Bergwijn - 5/10
Starting in a central role rather than in his usual spot on the wings, Bergwijn didn't look comfortable at all. He eventually got replaced by Kane.
Erik Lamela - 8/10
Lamela was excellent in this game. He worked his socks off, dribbled really well, and eventually got Spurs back in the game with a neat finish for the equaliser.
Pierre-Emile Hojbjerg - 6/10
After replacing Fernandes, Hojbjerg added to Spurs' defensive steel in midfield. He gave Mourinho's side a lot more calm and possesion. He also calmly tucked away his penalty in the shootout.
Harry Kane - 6/10
He had only one chance in regulation time. After doing well to create space for himself on his left foot, Kane fired a shot over the bar. He scored a penalty in the shootout as well.
Lucas Moura - 6/10
Lucas provided energy and flair down the left flank as Spurs went for the kill in the last few minutes. Helped Spurs put the pressure on. Scored his penalty.