Carabao Cup Second Round Draw Revealed: Chelsea and Tottenham Discover Their Next Challengers

Eleven Premier League clubs were included in Monday's second round draw for the 2026–27 Carabao Cup, with Chelsea and Tottenham Hotspur headlining the list of notable participants.

Chelsea were drawn against League One outfit Luton Town, managed by ex-Arsenal midfielder Jack Wilshere, in a fixture that will mark Xabi Alonso's first competitive home game in charge of the Blues.

Tottenham, meanwhile, face a London derby against Charlton Athletic in Roberto De Zerbi's first cup assignment with the club.

2026–27 Carabao Cup Second Round Draw in Full

North Draw

South Draw

When Is the Second Round of the 2026–27 Carabao Cup?

Exact dates for the Carabao Cup second round ties are yet to be confirmed, though all matches are pencilled in for the week of Aug. 24. With the Premier League kicking off just before that window, the cup games are expected to take place midweek.

This creates a potential scheduling headache for Chelsea, whose Premier League curtain-raiser away to Fulham is already set for Monday, Aug. 24. As a result, their cup clash with Luton is likely to be moved to Thursday — the same day Fulham's own tie against AFC Wimbledon would need to be played.

Complicating matters further, local policing rules typically prevent Chelsea and Fulham from hosting home matches on the same day due to their proximity. Fixture planners will need to navigate these constraints around an already congested Premier League schedule.

When Do the Remaining Premier League Teams Join the Carabao Cup?

Entering the Carabao Cup at this early stage is hardly a badge of honour for Chelsea or Tottenham.

In fact, only Premier League clubs that failed to secure a place in European competition this season are required to participate from the second round onwards.

Nine English clubs have earned spots in either the Champions League, Europa League, or Conference League, and those sides will not enter the Carabao Cup until the third round.

English Clubs in Europe This Season