Chelsea and Tottenham in the Carabao Cup: A Fresh Start

Chelsea and Tottenham are back in the Carabao Cup early – and that, in itself, tells a story.

Last season’s limp league finishes, 10th for Chelsea and 17th for Tottenham, have stripped both London clubs of European football. No Champions League nights, no Thursday trips abroad. Instead, they step into English football’s secondary cup competition at the second round, a stage they usually watch from a safe distance.

They will not be alone. Eleven Premier League sides enter at this point, joining 35 survivors from the opening round. Chelsea, Tottenham, Brentford, Fulham, Newcastle, Everton, Leeds and Nottingham Forest are all in the hat, along with newly-promoted Coventry, Ipswich and Hull. For some, it’s a chance to rotate and experiment. For others, it’s a route to relevance and a rare shot at silverware.

A reshaped start to the competition

The Carabao Cup itself has shifted gear this year. The first round began before the new EFL season even kicked off, and instead of the familiar midweek grind, most ties have been pushed onto a weekend.

The reasoning is blunt: too many games, too early. Clubs were being asked to play three times in a week at the very start of a campaign, and something had to give. This time, the early rounds carry a slightly different rhythm, the calendar eased just enough to keep legs fresher and managers slightly less agitated.

The action has already produced a jolt. Fourth-tier Walsall stunned Championship side Bristol City 1-0 at Ashton Gate on Thursday night to launch the competition in earnest, after Crawley and Rochdale had navigated preliminary meetings with York and Tranmere. A reminder, right away, that this is a cup where reputations can be shredded in 90 minutes.

When and where the draw happens

Attention now turns to the draw for the second round, which will shape the early storylines for Chelsea, Tottenham and the rest.

It takes place on Monday, August 10, 2026, during the build-up to the Devon derby between Plymouth and Exeter at Home Park. The draw is scheduled for around 7:20pm BST, with Sky Sports presenter David Prutton overseeing proceedings and former pros Jobi McAnuff and Jamie Mackie pulling out the balls.

The broadcast will run on Sky Sports Main Event, Sky Sports Football and Sky Sports Ultra HDR, with Sky Sports subscribers able to stream the draw via the Sky Go app. For those who prefer text to television, Standard Sport will carry a live blog as the ties are announced.

The competition remains regionalised for now. The first and second rounds are split into north and south sections, limiting travel and feeding local rivalries before the draw opens up from the third round onwards.

Ball numbers for the second round will be confirmed once the bulk of the first-round fixtures are completed over the weekend. Only then will clubs and supporters start plotting routes to Wembley in earnest.

The missing heavyweights

The Carabao Cup trophy currently sits in Manchester City’s cabinet, and the holders, like several of the league’s heavyweights, are still waiting in the wings.

City, Arsenal, Manchester United, Aston Villa and Liverpool all enter the Champions League this season. Bournemouth, Sunderland and Crystal Palace are in the Europa League, with Brighton in the Conference League. Those nine sides skip the early traffic and do not join the competition until the third round next month.

At the other end, the three clubs relegated from the Premier League last season – West Ham, Burnley and Wolves – have to start from the first round, a sobering reminder of how quickly status can flip in English football.

What comes next

Second-round ties will be played in the week commencing August 24, when the competition returns to its more traditional midweek slot. By then, league campaigns will be up and running, squads stretched, and managers forced into early-season decisions about priorities.

For Chelsea and Tottenham, the equation is stark. No European distractions, an early entrance, and a domestic cup that suddenly feels more significant than usual. Do they treat it as a proving ground for fringe players, or as a fast track to a much-needed trophy?

The draw on that Monday night in Devon will offer the first clue as to how bold they dare to be.