Chelsea and Tottenham Enter Carabao Cup Early
Chelsea and Tottenham will step back into the Carabao Cup spotlight tonight, but far earlier than either club would have planned.
There is no European safety net this season, no Thursday-night trips to the continent to soften the blow of last year’s underachievement. Tenth place for Chelsea, 17th for Tottenham: those finishes drag both London giants into the second round, a stage they have grown used to watching from afar.
Big hitters, early entrance
They are not alone. Eleven Premier League clubs in total drop into the competition at this point, joining 35 survivors from a first round that has already claimed its share of scalps.
Chelsea, Tottenham, Brentford, Fulham, Newcastle, Everton, Leeds and Nottingham Forest are all in the hat, joined by newly-promoted Coventry, Ipswich and Hull. Between them, they bring money, expectation and, in some cases, a clear need for silverware to steady a project that has wobbled.
The contrast with the elite is stark. Holders Manchester City, along with Arsenal, Manchester United, Aston Villa and Liverpool, are all tied up with Champions League commitments. Bournemouth, Sunderland and Crystal Palace are preparing for Europa League nights. Brighton have the Conference League. Those nine clubs will not touch the Carabao Cup until the third round next month.
Chelsea and Spurs cannot wait that long. Their season starts here.
Draw night drama in Devon
The draw for the second round takes place tonight, Monday August 10, 2026, in 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 guiding proceedings and former pros Jobi McAnuff and Jamie Mackie pulling the numbers that could shape the early weeks of the campaign.
It is a familiar ritual, but the stakes feel slightly different this time. With no European distraction, domestic cups take on a sharper edge. An awkward away tie on a tight lower-league pitch, a long midweek journey, a rotated XI that goes wrong – it can all set the tone.
The competition remains regionalised at this stage, split into northern and southern sections for both first and second rounds. Only from the third round does the draw open up fully, inviting the prospect of heavyweight clashes and storylines that carry through the winter.
Where to watch it unfold
The draw will be broadcast 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 pairing as it happens.
For clubs like Chelsea and Tottenham, the cameras and the commentary are a reminder: this is not a gentle warm-up. This is an early examination.
Who’s already through?
The first round has already carved a path for a mix of familiar names and ambitious underdogs.
In the Northern Section, Wolves swept past Port Vale 3-0, Sheffield United cruised to a 3-0 win at Mansfield and West Brom thumped Rotherham 4-1. Middlesbrough edged Wrexham 1-0, while Lincoln stunned Derby with a 2-1 away win. Blackburn won at Burton, Blackpool triumphed 3-1 at Grimsby, and Sheffield Wednesday, Fleetwood, Crewe, Stoke and Bradford all booked their places with regulation victories.
Penalty shootouts added the early-season jeopardy this competition thrives on. Barnsley squeezed past Wigan 6-5 on spot-kicks after a 1-1 draw, Stockport fell to Doncaster on penalties, Burnley survived a scare against Notts County with a 4-3 shootout win, Preston edged Huddersfield, and Shrewsbury came through at Salford.
In the Southern Section, Norwich sent a message with a 4-1 dismantling of MK Dons, while Southampton eased through with a 2-0 win at Colchester. West Ham, one of last season’s relegated trio, began their road back with a 3-1 victory over Portsmouth. Cardiff edged a five-goal thriller against Swindon, Birmingham shocked Swansea away from home, and Luton’s 3-0 win at Gillingham underlined their intent.
Again, penalties played their part. Millwall knocked out QPR at Loftus Road after a 1-1 draw, Reading survived at Bromley, and AFC Wimbledon held their nerve against Newport. Walsall, Stevenage, Cambridge, Peterborough, Watford, Leyton Orient, Charlton and Leicester all moved safely into the second round.
Plymouth’s clash with Exeter will complete the first-round picture tonight, right alongside the draw itself.
What comes next
Ball numbers for the second round will be confirmed once the bulk of the first-round ties are complete, finalising the cast list before the names are paired.
Second-round matches will be played in the week commencing August 24, back in the more traditional midweek slot that has long defined this competition’s rhythm.
For some clubs, the Carabao Cup will be a proving ground for youngsters and fringe players. For others, it will be the clearest, quickest route to a trophy. For Chelsea and Tottenham, entering earlier than they would like, it might just be a test of how quickly they can turn last season’s disappointment into something more convincing.
When the balls start rolling in Devon tonight, we will find out who gets the first real look at their resolve.
