For much of the contest, little separated the two sides. In the opening period, Cole Palmer and Jordan Henderson forced Antonin Kinsky into good saves. Mike Penders, meanwhile, produced good stops to deny Omar Marmoush and Mathys Tel.
The second period remained tight, but with 13 minutes to play, a Tottenham corner ended up in the Blues' goal via the hand of Penders, who was put under pressure by Jan Paul van Hecke.
Palmer was then shown a red card after receiving two yellows inside ten minutes, and Tel netted late on for Tottenham to condemn the Blues to defeat.
Two changes
Xabi Alonso was forced to make two changes to his starting XI. Emi Martinez and Joao Pedro both missed out due to injuries –the latter sustaining an issue in training yesterday – and were replaced by Penders and Geovany Quenda.
The opening 45 minutes were played in a downpour. It meant every touch had to be precise and every pass weighted perfectly. The Blues looked more threatening in the early stages and kept Tottenham at arm's length.
Our first chance of note was fashioned as the game approached the quarter-hour mark. Pedro Neto started it as he won the ball near the corner flag and fed it to Morgan Rogers inside the box. The England international laid it first-time to Palmer, who whipped his shot to the far post from an acute angle. However, Antonin Kinsky saved well.
Double save
As the half progressed, Spurs took a stranglehold of possession. Mohammed Kudus had the visitors' first shot of the evening – an attempt from inside the box that flew wide – before a good chance was created for Omar Marmoush from 10 yards. Penders reacted quickly to produce an excellent stop.
The Belgian goalkeeper produced an even better save soon after, rushing out and diving at the feet of Mathys Tel to deny the forward's left-footed strike.
Blues come close
Alonso's side responded to the Spurs' attempts. The first came following a mistake from Kinsky, which enabled Neto, Rogers and Palmer to exchange one-touch passes in the Tottenham penalty area and lay the ball to Henderson.
The Blues midfielder attempted to guide his finish into the corner, but put it close enough to Kinsky to allow the goalkeeper to save. Rogers was next denied as he drove a left-footed strike at goal, but the offside flag was subsequently raised.
Our final chance of the half fell to Neto, with a free-kick worked short to the Portuguese winger. He drove his shot to the near post, yet Kinsky got down to save and the game was goalless at the interval.
Searching for superiority
The Blues have often made fast starts to second halves this season, but both sides nullified each other's threat in 15 minutes after the break. Much of the game was played in midfield, with attacks breaking down or being snuffed out.
It wasn't until the hour mark that a shot was registered that threatened to break the deadlock. It came from Neto, who, after winning the ball and finding Palmer, reacted quickest to a rebound inside the area and drove a shot at Kinsky. The Tottenham stopper beat it behind for a corner.
Our first change of the afternoon came soon after, with Marco Palestra coming on for Hato. The Italian dropped into a role on the left of our defence. Estevao's introduction followed; he replaced Quenda.
Before the Brazilian's introduction came the game's biggest flashpoint. After Caicedo launched a counter-attack and was fouled in the process by van de Ven, a run from Palmer was halted by Mateus Fernandes falling and grabbing the ball. Several players came together, and three yellow cards followed, one of which went to Palmer.
From the restart, we fashioned an opportunity as Palmer and Henderson combined to get Estevao in on goal from a tight angle. He fired at goal but into the side netting.
Falling behind
With 13 minutes to play, and somewhat against the run of play, Tottenham went ahead. A corner was delivered into the Chelsea penalty area and van Hecke put Penders under pressure. The ball struck the hand of the Blues goalkeeper and deflected into our net despite Maxence Lacroix's efforts.
Our task got harder as, three minutes later, Palmer caught Conor Gallagher in midfield and referee Chris Kavanagh deemed it worthy of a second yellow card, and a red followed.
The game was effectively killed late on as a run and finish from Tel gave Tottenham a two-goal advantage in the closing stages, which they were able to see out to claim victory.
What comes next...
The Blues are back in action on Wednesday evening as we take on Liverpool in the fourth round of the Carabao Cup.
The teams
Chelsea: Penders; Acheampong, Lacroix, Colwill, Hato (Palestra 65); Caicedo (c), Henderson; Neto (Welbeck 88), Palmer, Quenda (Estevao 72); Rogers
Chelsea substitutes: Sharman-Lowe, Gusto, Fofana, Barco, Nicoll-Jazuli, Lavia
Booked: Palmer 71, Neto 79, Rogers 90+1
Sent off: Palmer 80
Tottenham Hotspur: Kinsky; Gray, van Hecke, van de Ven, Robertson (Pedro Porro 65); Mateus Fernandes, Tonali; Kudus (Kulusevski 89), Maddison (Gallagher 51), Tel (Davies 89); Marmoush (Solanke 65)
Tottenham Hotspur substitutes: Dubravka, Senesi, Olusesi, Williams-Barnett
Goalscorers: Penders og 77, Tel 87
Booked: Gallagher 67, van de Ven 71, Mateus Fernandes 72
Referee: Chris Kavanagh
