Chelsea and Tottenham Enter Carabao Cup: A New Challenge

Chelsea and Tottenham usually arrive late to this party. This year, they’re slipping in through a side door.

Stripped of European football after finishing 10th and 17th in the Premier League last season, the London rivals enter the Carabao Cup at the second round, a stage they once treated as someone else’s problem. No Champions League lights, no Thursday-night trips abroad. Just the raw, unvarnished grind of domestic cups and the league.

They won’t be alone. Eleven Premier League clubs drop in at this point, joining 35 first‑round survivors. Chelsea, Tottenham, Brentford, Fulham, Newcastle, Everton, Leeds and Nottingham Forest are all in the hat, along with newly-promoted Coventry, Ipswich and Hull. The glamour names with European commitments stay away for now; the rest get to work.

A Cup with a New Shape

Even the competition itself looks different this season. The Carabao Cup has crept forward in the calendar, with the first round kicking off before a ball is struck in the new EFL campaign and largely played over a weekend rather than its traditional midweek slot.

This is the fixture list talking. Clubs had grown used to a chaotic early-season schedule, cramming three matches into a week while players were still building fitness. The reshuffle aims to ease that strain, or at least spread it out more sensibly.

The ball is already rolling. Fourth-tier Walsall stunned Championship side Bristol City 1-0 at Ashton Gate on Thursday night to open the competition in earnest, a classic early-round upset to set the tone. Before that, Crawley and Rochdale had navigated preliminary ties against York and Tranmere.

The message is familiar: take this competition lightly, and it will bite.

When and Where the Draw Happens

The second-round draw arrives on Monday, August 10, 2026, slotted 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 Jobi McAnuff and Jamie Mackie handling the draw itself.

Sky Sports will show it live on Main Event, Football and Ultra HDR, with subscribers able to stream it through Sky Go. For those glued to their phones, Standard Sport will run a live blog charting every ball pulled.

One detail remains old-fashioned: the regional split. The Carabao Cup stays divided geographically for the first and second rounds, only opening up nationally from the third round onwards. That means familiar journeys and local edge before the wider field converges.

Who Waits, Who Walks In Later

While Chelsea and Tottenham prepare to re-enter a competition that has often offered them a shortcut to silverware, others must start even earlier. West Ham, Burnley and Wolves, all relegated from the Premier League last season, enter in the first round and must fight their way through if they want a shot at the top-flight scalps.

At the other end of the spectrum sit the holders and the heavyweights. Manchester City currently own the trophy and, like Arsenal, Manchester United, Aston Villa and Liverpool, step into this season’s edition at the third round because of their Champions League commitments. Bournemouth, Sunderland and Crystal Palace are tied up with the Europa League, while Brighton face a Conference League campaign. Those nine clubs stay out of the draw on Monday night and will not “join the party”, as the cliché goes, until next month.

Ball numbers for the second-round draw will be confirmed once the bulk of this weekend’s first-round ties are out of the way. Only then will the full picture emerge.

What is clear already is the schedule. Second-round ties will be played in the week commencing August 24, back in that familiar midweek window that has long belonged to the League Cup.

For Chelsea and Tottenham, that week brings more than just another fixture. It offers something they badly need: an early route to momentum, a shot at a trophy, and a chance to prove that last season’s slide was a detour, not a new direction.