Chelsea and Tottenham Enter Carabao Cup Second Round

Chelsea and Tottenham are back in the Carabao Cup earlier than they ever wanted to be. That’s the reality of finishing 10th and 17th in the Premier League: no European nights, no glamour trips, and an August date with a domestic cup that suddenly feels more important than usual.

This season, the London rivals step in at the second round, alongside a pack of Premier League sides trying to reset their stories. The competition offers something simple but powerful: a chance to win something, quickly, and to change the mood around a club long before winter bites.

A new-look start to the Carabao Cup

The Carabao Cup itself has been shuffled. The first round began before a ball was kicked in the new EFL campaign, and most of it has been played across a weekend, not the traditional midweek graveyard slot. The calendar has forced the change. Clubs were being asked to play three times in a week before their seasons had even found a rhythm; now, at least, the load is a little lighter.

The football, though, has lost none of its edge. Fourth-tier Walsall set the tone on Thursday night, walking into Ashton Gate and knocking out Championship side Bristol City 1-0. Crawley and Rochdale had already survived their preliminary tests against York and Tranmere. The message was clear before the big boys even arrived: this competition still bites.

Now the second round looms, and with it, the arrival of the Premier League’s middle class and strugglers.

When and where the draw happens

The draw for the second round will be made on Monday, August 10, 2026, in the build-up to the Devon derby between Plymouth and Exeter at Home Park. It is due to start at around 7:20pm BST.

Sky Sports will wrap the whole thing in its usual theatre. Presenter David Prutton will host, with Jobi McAnuff and Jamie Mackie pulling out the balls that could send Chelsea to a tricky away day or hand Tottenham a potential banana skin of their own.

The draw will be shown live on Sky Sports Main Event, Sky Sports Football and Sky Sports Ultra HDR, with Sky Go carrying the stream for subscribers. For those glued to their phones rather than their TVs, Standard Sport will chart every twist in a live blog.

Who joins at this stage?

Eleven Premier League clubs enter now, joining the 35 first-round winners. Chelsea and Tottenham headline that group, but they are far from alone.

• Brentford and Fulham step in.
• Newcastle arrive with expectations of pushing on again.
• Everton, still trying to claw their way back to stability, are in the hat too.
• So are Leeds and Nottingham Forest, each with their own ambitions and anxieties.

Then there is the newly-promoted trio: Coventry, Ipswich and Hull. For them, the Carabao Cup offers a different kind of test, a chance to measure themselves against established top-flight sides and to ride the momentum of promotion into a knockout setting.

Not everyone gets the relative luxury of a second-round start. West Ham, Burnley and Wolves, all relegated from the Premier League last season, have been thrown straight into the first round. There is no soft landing for those who fall out of the top flight.

At the other end of the spectrum, the elite wait. Holders Manchester City, along with Arsenal, Manchester United, Aston Villa and Liverpool, are tied up with Champions League commitments. Bournemouth, Sunderland and Crystal Palace have Europa League campaigns to juggle, while Brighton head into the Conference League. Those nine clubs won’t touch the Carabao Cup until the third round next month.

Regional split and the road ahead

For now, the competition remains regionalised. The first and second rounds are split geographically to cut down travel and add a bit of local spice, before the draw opens up completely later on. That means Chelsea and Tottenham can expect opponents from their half of the country, with the prospect of awkward away trips and feisty derbies never far away.

Ball numbers for the second round will be confirmed once the bulk of the first-round ties are done this weekend. Only then will clubs know exactly what to look for when the cameras roll at Home Park.

Once the draw is made, attention will turn quickly to the pitch. Second-round ties are scheduled for the week commencing August 24, back in the familiar midweek slot. By then, league campaigns will be under way, squads will already be stretched, and managers will be weighing rotation against the need for momentum.

For Chelsea and Tottenham, stripped of European fixtures and stripped of excuses, this competition offers something stark: a shot at silverware, and a chance to change the narrative of their seasons before it settles into something far less forgiving.