Chelsea boast an impressive record against their London rivals, but not so much in the League Cup, where they've only beaten them once in their last three meetings.
After edging past Brentford in the previous round, Thomas Tuchel's side know they will need a strong opening leg at home if they are to book themselves a place in next month's final.
As for Tottenham, they travel to Stamford Bridge off the back of an impressive 2-1 win over West Ham in the quarter-finals. With Antonio Conte now starting to settle in, he'll be gunning for his first trophy as Spurs boss.
Where, when and how to follow
Where: Stamford Bridge, London
When: Wednesday January 5, 19.45 GMT
Best tips for Chelsea vs Tottenham
Chelsea haven't had the best of luck at home recently, with four of their last five games at Stamford Bridge ending in draws.
The latest came in their fascinating match-up with Liverpool, where they fought back from 2-0 down to take a point.
They'll need to improve if they are to build up a first-leg lead in this tie, but it'll be a difficult task against a resolute Spurs side that have conceded just four goals in their last six games.
Still, there's no denying that it's Chelsea who have been the better team this season, and the odds reflect that, with the Blues favourite to win inside 90 minutes at 20/21, while Spurs can be backed at 15/4.
He is expected to return to the squad for the semi-final, though, and will have a point to prove.
As for Spurs, Conte has had an immediate impact since his arrival in north London, and even though they faltered in Europe, they've been superb domestically.
The England captain has scored three in his last five games - a huge improvement on his early season form. He'll be wanting to make up for lost time, and there's no better way to do that than to help fire his side towards a cup final.
Therefore, with both squads filled with goals, we can expect to see plenty scored on Wednesday night. I expect both defences to be rotated and that will have the forwards licking their lips.
It's a London derby with a place in a final up for grabs, so we can expect fireworks. With that in mind, it's worth considering Planet Sport Bet's boosted 5/2 offer on over 3.5 total match goals.
Last 10 head-to-head
Chelsea wins: 6
Spurs wins: 3
Chelsea goals: 14
Spurs goals: 7
A feisty history
Wednesday night will write the next chapter of this historic London derby, and regardless of where these sides meet, it usually ends in drama.
Cast your minds back to when these two met in 2016, in a match since coined 'The Battle of the Bridge'. Tottenham were going toe-to-toe with Leicester City for the title, but reigning champions Chelsea stood in their way.
Spurs knew a win was needed to keep up their title hopes, while Chelsea desperately wanted to put an end to their chances. What followed was a match of unrivalled intensity, resulting in a remarkable 12 yellow cards.
It's not just a one-off either. In their last six meetings there's been a hefty 26 yellow cards and one red - Heung-min Son's dismissal in December 2019.
With an evenly matched game expected on Wednesday, there's every chance it could again descend into chaos, which makes the booking market an extremely enticing option.
Planet Sport Bet is offering 20/21 for over 4.5 total match cards, which is certainly worthy of our attention given the storied history of this fixture.
An impeccable home record
While it is bound to be a well-balanced tie, Chelsea get my nod as the eventual winners due to their dominant home form against Spurs.
The Blues have only lost one of their last 33 home games against them, with that one defeat coming in 2018 when Dele Alli's brace proved to be the difference.
It has continued to be a difficult place for Spurs to visit, with only one draw to show from their last three trips.
With that said, turning towards Chelsea to win inside 90 minutes is logical, and at around evens it holds good value too.
Goalscorer bets for Chelsea vs Tottenham
As mentioned before, Harry Kane is getting back to somewhere near his best form, and at 7/4 he is a good punt as an anytime goalscorer.
Kane has scored six goals in 17 appearances against Chelsea, including one in the last meeting between these two sides in a League Cup semi-final.
As for Chelsea, Marcos Alonso is a tempting option at 6/1. The Blues have played most of the season without a focal point up front, and as a result their goals have been spread throughout the squad.
Most of them have been shared between the wing-backs, with Tuchel instructing his wide men to push forward as often as they can.
Alonso appears to be most likely to be operating down Chelsea's left flank, and the Spaniard has a keen eye for goal.
He's also racked up three goals against Spurs in 11 appearances, making his 6/1 odds look big.