West Ham beat Portsmouth 3-1 on Saturday to book their place in the Carabao Cup second round, with Chelsea and Tottenham now entering the competition as the draw takes place tonight at approximately 7:20pm BST on Sky Sports Main Event.
Valentin Castellanos scored twice as the Hammers came from behind, with Jarrod Bowen also finding the net to complete a convincing result in front of the largest-ever crowd at a Carabao Cup first-round match. The win gave West Ham a positive start to the new season, arriving two months after their relegation from the Premier League.
Chelsea, managed by Xabi Alonso, come into the draw having failed to qualify for Europe last term, with the cup offering an early opportunity to pursue silverware. Tottenham, who finished 17th in the 2025-26 Premier League campaign and only narrowly avoided the drop, are also in the hat. Both clubs last featured at this stage when Spurs were knocked out on penalties by Fulham and Chelsea defeated AFC Wimbledon before going on to reach the final at Wembley, where Liverpool beat them.
Newcastle, who won this trophy in 2025, are among the other top-flight sides awaiting their fate, along with Everton, Leeds and Nottingham Forest. Wolves and Burnley, like West Ham relegated from the Premier League last season, have also progressed. Wolves won 3-0 against Port Vale, while Burnley needed a penalty shootout to eliminate Notts County, with Kyle Walker scoring the decisive spot kick at Turf Moor.
Elsewhere in the first round, Millwall goalkeeper Lukas Jensen made a remarkable return to action after 15 months out injured by saving all four of QPR's penalties in a shootout at Loftus Road. Bristol City were beaten at Ashton Gate by League Two Walsall, and Middlesbrough knocked out Wrexham. Norwich and West Brom both scored four goals in their respective ties to advance in style.
The draw remains split into north and south sections to ease midweek travel demands, meaning London clubs — among them Chelsea, Tottenham, West Ham, Brentford, Fulham, Charlton, Leyton Orient, Millwall and AFC Wimbledon — could be drawn against each other, making at least one derby a strong possibility. That regionalised format applies to the second round only; the third round will be open.
David Prutton hosts the draw on Sky Sports, with Jamie Mackie and Jobi McAnuff pulling the teams from the hat during the build-up to Plymouth Argyle's first-round clash with Exeter City — the one side who will not yet know their second-round opponent once the draw is made. The draw is also available to watch for free on the Sky Sports Football YouTube channel.
Reporting: Mirror, Football.London, Evening Standard, The Independent.