Chelsea and Tottenham Face Carabao Cup Draw Tonight

Chelsea and Tottenham will discover their Carabao Cup fate tonight, and the timing says everything about where they are right now.

Two of English football’s heavyweight brands, both entering the League Cup in the second round. Not as reward, but as punishment for last season’s limp Premier League finishes — 10th for Chelsea, 17th for Spurs, and no European football between them. The price of mediocrity is an early midweek trip to an unglamorous away ground. That reality lands this evening.

Early entry, early pressure

The second-round draw takes place tonight, Monday August 10, 2026, in the build-up to the Devon derby between Plymouth and Exeter at Home Park. It is slated for around 7.20pm BST, with Sky Sports presenter David Prutton fronting the coverage and former pros Jobi McAnuff and Jamie Mackie pulling out the balls.

It is a familiar ritual, but with a different edge this time. Chelsea and Tottenham are not waiting around for the third round like the continent-bound elite. They are in the pot with the rest of the also-rans, hoping the first step on a domestic cup run does not turn into an early embarrassment.

The Carabao Cup remains regionalised at this stage, split into northern and southern sections for the first and second rounds, so both London clubs will be kept local for now. The glamour ties, the big cross-country trips and the heavyweight clashes come later. This round is about avoiding a headline for the wrong reasons.

Who joins the party?

Chelsea and Spurs are two of 11 Premier League clubs entering at this point. Brentford, Fulham, Newcastle, Everton, Leeds and Nottingham Forest are in the same boat, along with newly-promoted trio Coventry, Ipswich and Hull.

They join the 35 winners from the first round, where the competition has already started to bite. Wolves, Burnley and West Ham — all relegated from the Premier League last season — had to begin there and have already navigated potential slip-ups. Wolves brushed aside Port Vale 3-0, Burnley needed penalties to edge out Notts County after a 1-1 draw, and West Ham beat Portsmouth 3-1 in the southern section.

Across the rest of the north, Middlesbrough squeezed past Wrexham 1-0, Sheffield Wednesday edged Bolton by the same score, and Sheffield United cruised to a 3-0 win at Mansfield. Blackburn won 2-1 at Burton, West Brom thumped Rotherham 4-1, while Lincoln stunned Derby 2-1 at Pride Park. Several ties went to penalties: Barnsley beat Wigan 6-5, Doncaster knocked out Stockport, Preston saw off Huddersfield, and Shrewsbury survived at Salford.

In the southern half of the draw, Walsall shocked Bristol City 1-0, Stevenage won at Wycombe, and Cambridge beat Barnet 2-1. Millwall dumped out QPR on penalties at Loftus Road, Luton swept past Gillingham 3-0, and Cardiff edged a five-goal thriller against Swindon. Watford beat Crawley 1-0, Norwich hammered MK Dons 4-1, and Southampton eased past Colchester 2-0. Birmingham claimed a 1-0 win at Swansea, Charlton won 3-1 at Cheltenham, and Reading survived a shootout at Bromley.

One tie remains outstanding: Plymouth vs Exeter, the Devon derby that doubles as the stage for tonight’s draw.

The big guns wait

While Chelsea and Tottenham prepare to step back into a competition that has often defined their seasons, the current holders and the European contingent stay on ice.

Manchester City, who currently own the trophy, are among nine clubs not entering until the third round. City, Arsenal, Manchester United, Aston Villa and Liverpool are all in the Champions League this season. Bournemouth, Sunderland and Crystal Palace head into the Europa League, with Brighton in the Conference League.

Those nine clubs do not touch the Carabao Cup until next month. Tonight is about everyone else — the teams who know a domestic cup can rescue a season, or at least change its mood.

How to follow the draw

The draw will be shown live on Sky Sports Main Event, Sky Sports Football and Sky Sports Ultra HDR. Sky Sports subscribers can also watch it via the Sky Go app. For those who prefer text and reaction as it happens, Standard Sport will run a live blog throughout the draw.

Second-round ties are scheduled for the week commencing August 24, back in the familiar midweek slot that has long defined this competition.

By then, Chelsea and Tottenham will know whether their route back to respectability starts with a routine assignment or a trip that tests their nerve. After last season’s bruises, neither can afford to treat this as just another cup night.