According to a report by BBC Sport on Saturday, October 17, 2026, Chelsea are preparing for a challenging run of fixtures as the 2026/2027 season progresses, with Xabi Alonso’s side set to face Tottenham Hotspur, Liverpool and Manchester United in important matches across the Premier League and Carabao Cup.

The Blues will head into the upcoming fixtures with confidence following their impressive 5-1 Premier League victory over Bournemouth on October 10.

Chelsea’s demanding schedule begins with a London derby against Tottenham Hotspur before they travel to Anfield to face Liverpool in the Carabao Cup. They will then return to Stamford Bridge to host Manchester United in another crucial league encounter.

Chelsea vs Tottenham Hotspur

Competition: Premier League

Date: Saturday, October 24, 2026

Venue: Stamford Bridge

Kick-off: 5:30 pm UK time

Chelsea will welcome Tottenham to Stamford Bridge for a London derby that could have important implications for their Premier League campaign.

Alonso’s team will aim to take advantage of playing at home, while Tottenham will be determined to secure a positive result. Chelsea will need to maintain their defensive organisation and deliver a strong performance to overcome their rivals.

Liverpool vs Chelsea

Competition: Carabao Cup

Date: Wednesday, October 28, 2026

Venue: Anfield

Kick-off: 8:00 pm UK time

Chelsea will travel to Anfield to face Liverpool in the fourth round of the Carabao Cup.

The encounter presents another major challenge for Alonso’s players as they seek to advance to the next stage of the competition. Liverpool’s home advantage could make the tie difficult, requiring Chelsea to be clinical in attack and disciplined defensively.

Chelsea vs Manchester United

Competition: Premier League

Date: Saturday, October 31, 2026

Venue: Stamford Bridge

Kick-off: 12:30 pm UK time

Manchester United will visit Stamford Bridge for a highly anticipated Premier League clash.

Chelsea will be targeting all three points against one of their traditional rivals. However, the short turnaround following their Carabao Cup meeting with Liverpool could test the squad, forcing Alonso to manage his players carefully.

Sunderland vs Chelsea

Competition: Premier League

Date: Sunday, November 8, 2026

Venue: Stadium of Light

Kick-off: 2:00 pm UK time

Chelsea will travel to the Stadium of Light to face Sunderland in their next Premier League fixture after the Manchester United match.

The Blues will aim to continue collecting points but must remain focused against a Sunderland side capable of challenging visiting teams.

Chelsea vs Leeds United

Competition: Premier League

Date: Saturday, November 21, 2026

Venue: Stamford Bridge

Kick-off: 3:00 pm UK time

Chelsea will return to Stamford Bridge after the November international break to take on Leeds United.

The fixture will provide another opportunity for Alonso’s side to improve their position in the league table. The Blues will be expected to make the most of home advantage and deliver a convincing performance in front of their supporters.

Overall, Chelsea face a demanding period, with Tottenham, Liverpool and Manchester United presenting their immediate major challenges.

How Alonso manages the squad and navigates the short gaps between fixtures could prove important to Chelsea’s ambitions in both the Premier League and Carabao Cup. The next five matches will also provide a clearer indication of the team’s consistency and progress under the Spanish manager.