Blues manager Mauricio Pochettino will sit in the away dugout for the first time as a manager in N17 as he looks to reverse his side's form in the most unwelcome of surroundings. Pochettino oversaw Spurs' best period in decades during over five years in charge - culminating in a Champions League final - but returns as an enemy.
Ange Postecoglou, meanwhile, has taken his new squad to the top of the Premier League thanks to the best ever start to a season by a newly appointed manager. He will know another victory under the lights will be the most important of the lot, by a distance.
Date, kick-off time and venue
Tottenham vs Chelsea is scheduled for an 8pm GMT kick-off on Monday, November 6, 2023.
The match will take place at the Tottenham Hotspur Stadium in north London.
Where to watch Tottenham vs Chelsea
TV channel: In the UK, the game will be televised live on Sky Sports, with Monday Night Football coverage beginning at 6.30pm GMT ahead of an 8pm kick-off.
Live stream: Subscribers can also catch the contest live online via the Sky Go app and website.
Live blog: You can follow all the action on matchday via Standard Sport’s live blog, with expert analysis from both Dan Kilpatrick and Nizaar Kinsella.
Tottenham vs Chelsea team news
Speaking to reporters on Thursday, Postecoglou gave Destiny Udogie a "50-50" chance of being fit but noted there was still plenty of time for the left-back to further recover from a recent knock. Rather concerningly, deputy left-back Ben Davies has been ruled out of the game.
Yves Bissouma escaped a fifth yellow card of the season last time out, so should start in midfield alongside Pape Sarr. Rodrigo Bentancur continues to work back to full fitness after nine months out with a serious knee injury, but should make the squad after a late cameo in the win at Crystal Palace.
Brennan Johnson is pushing to replace Richarlison on the left-hand side of Spurs' attack.
For Chelsea, both Armando Broja and Mykhailo Mudryk remain doubts for the game. Pochettino will provide a fresh fitness update on the pair during Friday's press conference.
Elsewhere, Christopher Nkunku hopes to be back before the end of November but this game will come too soon. The same can be said for midfielder Romeo Lavia and Ben Chilwell. All other injuries are longer-term.
Tottenham vs Chelsea prediction
Spurs are clearly the team in form, they are top of the table after all while Chelsea have just three league wins all season and come into the game after yet another unconvincing display, albeit in victory, against lower-league Blackburn.
But, as the saying goes, the form book can go out the window in derbies. This one in particular - given the intense rivalry and Pochettino's return - will require the calmest of heads to come out victors. Chelsea could cause an upset but Postecoglou will have his players ready not to let the occasion get to them.
Tottenham to win, 2-1.
Head to head (h2h) history and results
Tottenham wins: 56
Draws: 42
Chelsea wins: 77
Spurs have won just one of the last nine Premier League derbies between these two teams after winning three of the previous four.
Tottenham vs Chelsea match odds
Tottenham: 10/11
Draw: 15/8
Chelsea: 11/5
Odds via Betfair (subject to change).