Chelsea and Tottenham Prepare for Carabao Cup Draw Tonight

Chelsea and Tottenham step back into the Carabao Cup tonight, not as European heavyweights easing in at the business end, but as early entrants with something to prove.

Tenth and 17th in last season’s Premier League. No European football. No hiding place. The price for those finishes is paid now, under the Monday night lights, as both clubs wait to discover their second-round opponents.

Early start for London’s fallen giants

The draw for the second round of this season’s Carabao Cup takes place tonight, Monday August 10, 2026, during the build-up to the Devon derby between Plymouth and Exeter at Home Park. It is scheduled to begin at around 7.20pm BST.

Sky Sports presenter David Prutton will host, with Jobi McAnuff and Jamie Mackie conducting the draw. Names, numbers, and a few sharp intakes of breath. For Chelsea and Tottenham, it is the first official marker of how long and how complicated this domestic season might become.

The competition remains regionalised for both the first and second rounds, so the London clubs know at least that their early journeys will be closer to home before the tournament opens up later on.

Who joins the hat?

They are not alone. Eleven Premier League clubs in total enter at this second-round stage, joining the 35 winners from the first round.

Alongside Chelsea and Tottenham come Brentford, Fulham, Newcastle, Everton, Leeds and Nottingham Forest, plus newly-promoted Coventry, Ipswich and Hull. All of them step in now, while the three clubs relegated from the Premier League last season – West Ham, Burnley and Wolves – had to start a step earlier in the first round.

At the other end of the spectrum sit the current holders, Manchester City. They, along with Arsenal, Manchester United, Aston Villa and Liverpool, are all tied up with Champions League commitments. Bournemouth, Sunderland and Crystal Palace are involved in the Europa League, with Brighton in the Conference League. Those nine sides do not touch the Carabao Cup until the third round next month.

So tonight’s draw is about the rest: the ambitious, the rebuilding, the sides looking for momentum and silverware while the continent’s distractions wait for others.

How to watch it unfold

The draw will be shown live on Sky Sports Main Event, Sky Sports Football and Sky Sports Ultra HDR.

Sky Sports subscribers can also stream it via the Sky Go app, while Standard Sport will run a live blog tracking every ball and every tie as they are announced.

One glance at the list of first-round results tells you how treacherous this competition can be. Wolves and Burnley are already through after comfortable wins over Port Vale and Notts County respectively. West Ham saw off Portsmouth. Sheffield United, Southampton, Norwich and others have already navigated their opening hurdles.

From late drama to penalty shootouts, the first round has already done its usual job of unsettling the complacent. Barnsley, Stockport, Salford, QPR and Bromley all saw their fates decided from the spot. That is the landscape Chelsea and Spurs now walk into.

When the real work begins

Ball numbers for the second-round draw will be confirmed once the bulk of the first-round ties are completed, including the remaining fixture between Plymouth and Exeter.

Second-round matches will be played in the week commencing August 24, back in the familiar midweek slot that has long defined this competition.

For some, the Carabao Cup is a proving ground for youngsters and squad players. For Chelsea and Tottenham this season, it feels like something more pointed: an early test of resolve, a chance to change the mood, a route – maybe the quickest one – back to a trophy lift under the glare of Wembley’s arch.