Chelsea and Tottenham Enter Carabao Cup: A Fresh Start
Chelsea and Tottenham will step through a side door into this season’s Carabao Cup, a reminder of how far both clubs fell last year and how quickly they must now reset.
Tenth and 17th in the Premier League. No European football. No Thursday nights under the lights on the continent. Instead, England’s secondary cup competition becomes an early proving ground, and the London rivals enter at the second-round stage, a round earlier than they have grown used to in recent years.
They will not be alone. Eleven Premier League clubs join the 35 first-round winners in round two, with Chelsea, Tottenham, Brentford, Fulham, Newcastle, Everton, Leeds and Nottingham Forest joined by newly-promoted Coventry, Ipswich and Hull. It is a different sort of company to the Champions League elite, but it is where the hard work starts.
Those elite sides wait their turn. Manchester City, Arsenal, Manchester United, Aston Villa and Liverpool, all bound for the Champions League, sit this round out. Bournemouth, Sunderland and Crystal Palace prepare for Europa League campaigns, while Brighton gear up for the Conference League. Those nine clubs do not touch the Carabao Cup until the third round next month, when the competition opens up and the heavyweights arrive.
For now, the focus is on the draw.
New look, old stakes
This season’s Carabao Cup has already shifted the furniture. The first round began even before the new EFL campaign kicked off and, instead of the usual midweek grind, most ties have been pushed onto a weekend. The aim is simple: ease the early-season logjam that has often forced clubs into three matches in seven days before their squads have even settled.
The ball has already started rolling. Fourth-tier Walsall stunned Championship side Bristol City 1-0 at Ashton Gate on Thursday night to open the competition with a jolt. Crawley and Rochdale had earlier navigated preliminary round ties against York and Tranmere, clearing their own paths into the main draw.
The structure retains one familiar quirk. The competition remains regionalised through the first and second rounds, splitting clubs into north and south to limit travel and stoke local tension, before the barriers come down from the third round onwards.
When and where the draw happens
The second-round draw takes place on Monday August 10, 2026, woven into the build-up to the Devon derby between Plymouth and Exeter at Home Park. It is scheduled for around 7:20pm BST, with Sky Sports presenter David Prutton fronting the coverage and former professionals Jobi McAnuff and Jamie Mackie handling the draw itself.
The Carabao Cup trophy currently sits in Manchester City’s cabinet, a familiar piece of silverware in a familiar setting. Clubs like Chelsea and Tottenham, stripped of European distraction, will see this competition as both opportunity and obligation: a realistic route to a trophy and a test of how quickly new managers, new signings and new ideas can gel.
Sky Sports will broadcast the draw live on Sky Sports Main Event, Sky Sports Football and Sky Sports Ultra HDR, with subscribers able to stream it via the Sky Go app. A live blog will track every ball as it’s pulled.
Ball numbers for the second round will be confirmed once the bulk of the first-round ties conclude over the weekend. Only then will Chelsea, Tottenham and the rest know exactly who stands in their way.
What comes next
Second-round ties will be played in the week commencing August 24, back in the more familiar midweek slot that has long defined this competition.
For some clubs, it will be an early chance to rotate. For others, it will be a lifeline. For Chelsea and Tottenham, starting a season without Europe for the first time in years, the Carabao Cup may quickly become more than a sideshow. How they treat it now will say plenty about what they expect from the months ahead.
