It has been three years since both teams entered this stage of the League Cup, having failed to qualify for Europe last season.
The London rivals, along with nine other Premier League teams, learn their fate tonight, while the nine top-flight teams with European commitments do not get involved until the third round.
So, could we see a blockbuster London derby in the second round?
Can Chelsea and Tottenham face each other in Carabao Cup second round?
Yes! Neither Chelsea or Tottenham will like it, but it is possible we will get a League Cup second-round derby.
Unlike the third round, which is seeded, there is no rule preventing the two biggest teams in the draw being drawn against each other.
In fact, the draw mechanics will see the draw again split into north and south sections – to prevent lengthy travel times – which, in turn, reduced the pool and heightens the chances of a Chelsea vs Spurs clash.
In previous years, the third round was seeded to preview teams competing in Europe facing each other. It was to aid the scheduling, rather than the teams with extra commitments.
Chelsea and Tottenham potential opponents
Chelsea and Tottenham will be in the southern section of the draw, so their list of possible opponents have been cut down by half.
Premier League: Brentford, Coventry City, Fulham, Ipswich Town, Chelsea/Tottenham
Championship: Birmingham City, Cardiff City, Charlton Athletic, Millwall, Norwich City, Southampton, Watford and West Ham
League One: AFC Wimbledon, Cambridge United, Leicester City, Leyton Orient, Luton Town, Peterborough United, Reading and Stevenage
To be confirmed: Plymouth Argyle or Exeter City
