Chelsea and Tottenham Prepare for Carabao Cup Challenge
Chelsea and Tottenham, two clubs used to circling the business end of major competitions, will step into the Carabao Cup tonight earlier than they ever wanted to.
Tenth and 17th in last season’s Premier League table. No European football. No late entry. The consequence is clear: both London sides are back in the domestic cups at the second-round stage, rubbing shoulders with clubs who normally watch the giants arrive a round later.
This is where their season starts to get serious.
Early Judgement Night
The second-round draw for the 2026-27 Carabao Cup takes place tonight, Monday August 10, during the build-up to the Devon derby between Plymouth and Exeter at Home Park. It is scheduled for around 7.20pm BST, live on Sky Sports, with David Prutton fronting the coverage and Jobi McAnuff and Jamie Mackie pulling the numbers that could shape the first months of Chelsea and Spurs’ campaigns.
The format is familiar, but the stakes feel different. With no European fixtures to navigate, this competition suddenly carries extra weight for clubs who must prove they can still live off more than history and ambition.
Chelsea and Tottenham are among 11 Premier League sides entering at this stage, joining the 35 first-round winners. Brentford, Fulham, Newcastle, Everton, Leeds and Nottingham Forest are also in the hat, along with newly-promoted Coventry, Ipswich and Hull.
The three clubs relegated from the Premier League last season – West Ham, Burnley and Wolves – have already been thrown into the grind, starting from the first round.
Europe Waits, the Cup Can’t
At the top of the food chain, the picture looks very different. Holders Manchester City, plus Arsenal, Manchester United, Aston Villa and Liverpool, are all in the Champions League. Bournemouth, Sunderland and Crystal Palace are bound for the Europa League, while Brighton step into the Conference League.
Those nine clubs skip this round entirely and will not touch the Carabao Cup until the third round next month. For Chelsea and Spurs, there is no such luxury. Their margin for error has shrunk.
The competition remains regionalised through the first and second rounds, split into northern and southern sections before opening up later on. That means the London clubs are looking at a familiar map: potential derbies, awkward away trips, and the kind of combustible ties that can ignite or derail a season before it has properly settled.
The Road So Far
The first round has already cleared a path for them.
In the Northern Section, Middlesbrough edged Wrexham 1-0, Wolves swept aside Port Vale 3-0, and Sheffield United cruised past Mansfield 3-0. West Brom thumped Rotherham 4-1, while Sheffield Wednesday, Stoke, Crewe, Bradford and Blackpool all booked their places. Penalties decided tight contests at Barnsley, Stockport, Burnley, Preston and Salford, with Lincoln, Blackburn and Shrewsbury also advancing.
In the Southern Section, Walsall stunned Bristol City 1-0, Luton eased past Gillingham 3-0, and Cardiff won a five-goal thriller against Swindon. Norwich hit four against MK Dons, Southampton handled Colchester 2-0, and West Ham – already in from the first round – beat Portsmouth 3-1. Millwall knocked out QPR on penalties, Birmingham edged Swansea 1-0, while Peterborough, Watford, Leyton Orient, Reading, Leicester, Charlton and AFC Wimbledon all progressed.
Plymouth vs Exeter will complete the picture before the draw is made.
Ball numbers for the second round will be confirmed once the bulk of those ties are finished, but the shape of the field is already clear: a mix of hopeful underdogs and wounded heavyweights, all funnelled into a midweek window that suddenly looks crucial.
A Different Kind of Pressure
The second-round fixtures will be played in the week commencing August 24, back in the familiar midweek slot that has long belonged to this competition.
For Chelsea and Tottenham, that week will not just be about rotation or minutes for fringe players. It will be a test of attitude. An early gauge of how seriously they are taking a season without European distraction. A chance to chase a trophy that has so often been a springboard for momentum, or a mirror held up to a squad’s shortcomings.
Tonight’s draw will not decide their season. But it will show them exactly how quickly they need to grow up in this new reality.
