As part of a hurried schedule following a late start to the campaign, this is the Blues' second Carabao Cup game in the space of a week, after a comfortable victory against Barnsley last Wednesday at Stamford Bridge.
As for Tottenham, their tie against Leyton Orient was abandoned following numerous positive Covid-19 cases amongst Leyton Orient players. On Friday , the FA confirmed that Tottenham would receive a bye to the next round due to Leyton Orient's cancellation.
Both sides come into the game off the back of disappointing Premier League results at the weekend, with Chelsea held to a 3-3 draw at the Hawthornes against West Bromwich Albion, and Tottenham dropping points at home to Newcastle United, drawing 1-1 thanks to a late controversial penalty for Newcastle which was dispatched by Callum Wilson.
Fellow summer signing Hakim Ziyech will remain sidelined with injury along with Christian Pulisic and Billy Gilmour, while Antonio Rüdiger, Marcos Alonso and Ruben Loftus-Cheek are all expected to miss out as they are expected to leave the club before the transfer window shuts next Monday.
Ben Chilwell is in line to make his first start for the club following his brief cameo against Barnsley last week, and is set to join substitutes from Saturday's draw against West Brom, Callum Hudson-Odoi, Cesar Azpilicueta and Olivier Giroud, from the off.
In regards to Tottenham, more team rotation is expected from boss Jose Mourinho. However, that will not mean a start for Dele Alli, as he is once again expected to be excluded from the 18 man squad with a potential move away from Tottenham on the cards.
After he was substituted at half time on Sunday against Newcastle, Son Heung-Min was confirmed to have suffered a hamstring issue which will see him sidelined, joining Japhet Tanganga, Moussa Sissoko and new signing Gareth Bale on the injury list.
However, recent acquisition Sergio Reguilón is in line to make his debut at left back in place of Ben Davies.
Tottenham Hotspur: Hart; Aurier, Alderweireld, Dier, Reguilón; Fernandes, Højbjerg, Ndombele; Lamela, Lucas, Bergwijn.
Chelsea: Mendy; Azpilicueta, Tomori, Zouma, Chilwell; Jorginho, Barkley, Mount; Havertz, Giroud, Hudson-Odoi.
Ones to Watch
This game is all about the two left backs: Chelsea's Ben Chilwell and Tottenham's Sergio Reguilón. Both set to make their first starts for their new clubs, both are coming in with high expectations on the shoulders and a good start to their careers at their new clubs would be a massive boost for both teams.
After arriving at the club injured, Chilwell made his first appearance last week against Barnsley as a substitute for Kai Havertz, and gave Chelsea fans a taste of things to come with a wonderful cross to assist Olivier Giroud's late goal. Chelsea have been crying out for a quick, solid left back with good delivery for a while, and in Chilwell they will be hoping that he's the one to fill the void.
Reguilón was a much sought after left back this summer after his impressive form on loan at Sevilla last season attracted the interest from clubs such as Manchester United and Chelsea. To sign a player of his ability was a real statement of intent for Tottenham, as he joined from Real Madrid for £28million. Replacing Danny Rose, who has been frozen out by Mourinho after 10 years as Tottenham's left back, many see the 23 year old as one of the best signings of the summer, and tonight is the first time we can see whether it was money well spent.
A lot of the most notable meetings between these sides has come in the Carabao Cup, and has really added an extra spark in the rivalry between them. Tottenham's last silverware that they won came in this competition in 2008, as Jonathan Woodgate's extra time header saw the beat Chelsea 2-1 at Wembley in the league cup final. Chelsea's revenge came in 2015, when they beat Spurs 2-0 in the final thanks to goals from John Terry and Diego Costa, under the management of current Spurs boss Jose Mourinho. However, their most recent meeting in the competition came in 2019, when Chelsea won 4-2 in the penalty shootout after a 2-2 aggregate score in semi-final, with David Luiz's penalty being the decider to send Chelsea through to the final.
Where to Watch
Tottenham Hotspur v Chelsea kicks off at 7:45pm BST tonight (29/09/20) and is available to watch on Sky Sports Main Event and Sky Sports Football from 7pm BST.