Chelsea and Tottenham Enter Carabao Cup Early
Chelsea and Tottenham are used to circling this competition from a distance in August, waiting for the European elite to filter in before joining the fray themselves. Not this year.
Mid-table finishes and the absence of European football have dragged both London clubs into the Carabao Cup at the second-round stage, a blunt reminder of how far they fell last season and how quickly they must respond.
London giants step in early
Chelsea, 10th in the Premier League last term, and Tottenham, who limped home in 17th, now stand alongside nine other top-flight clubs preparing to learn their fate in Monday’s second-round draw. Brentford, Fulham, Newcastle, Everton, Leeds and Nottingham Forest are there too, joined by newly-promoted Coventry, Ipswich and Hull.
It is a curious group: heavyweights trying to rebuild, ambitious mid-table sides sniffing a trophy, and promoted clubs eager to announce themselves.
The contrast with the absent nine is stark. Manchester City, Arsenal, Manchester United, Aston Villa and Liverpool are all tied up with the Champions League. Bournemouth, Sunderland and Crystal Palace head into the Europa League, while Brighton step into the Conference League. Those teams will not touch this competition until the third round next month.
For Chelsea and Spurs, there is no such luxury. No midweek European lights. No grand continental stage. The Carabao Cup suddenly feels less like a sideshow and more like an early test of credibility.
A reshaped start to the competition
Even the competition itself has shifted. The first round began before the new EFL season kicked off, with ties spread largely over a weekend rather than the usual midweek grind. The change is deliberate: a bid to ease the early-season congestion that has often forced clubs into three matches in seven days before their squads have even settled.
The action has already thrown up a jolt. Fourth-tier Walsall stunned Championship side Bristol City 1-0 at Ashton Gate on Thursday night, a result that set the tone after Crawley and Rochdale had navigated preliminary round meetings against York and Tranmere.
Cup football has not waited for the big names to arrive. It has already started biting.
When and where the draw happens
The second-round draw lands on Monday, August 10, 2026, dropped neatly into the build-up to the Devon derby between Plymouth and Exeter at Home Park. It is scheduled for around 7:20pm BST.
Sky Sports will turn it into an event of its own. Presenter David Prutton will host, with Jobi McAnuff and Jamie Mackie pulling the numbers that will map out the next step of the competition. The draw will go out live on Sky Sports Main Event, Sky Sports Football and Sky Sports Ultra HDR, with Sky Go carrying the stream for subscribers. Standard Sport will run a live blog for those who prefer every twist in real time.
Ball numbers for the second round will be confirmed once the bulk of the first-round ties are completed over the weekend, another small pause before the bigger clubs are thrown into the mix.
One thing does remain familiar: the regional split. The Carabao Cup stays divided geographically for the first and second rounds, only opening up fully from the third round onwards. Local grudges and shorter journeys first; the cross-country glamour comes later.
What’s at stake for Chelsea and Spurs?
For Manchester City, the current holders, this competition has become a habit. For Chelsea and Tottenham, it now looks like an opportunity.
With no European schedule to manage, both clubs face fewer excuses when it comes to rotation and focus. A domestic cup run can steady a dressing room, sharpen a manager’s authority and give new signings a platform. It can also expose fragility if the early rounds go wrong.
The second-round ties will be played in the week commencing August 24, when the competition slips back into its more traditional midweek slot. By then, the Premier League season will be finding its rhythm, and managers will have to decide how much of their hand to show.
For two London giants forced into an earlier entrance than they would like, the draw on Monday is more than just names in a bowl. It is the first marker of whether this season will be about recovery, or about another year of regret.
