Chelsea are preparing for a hectic period of football across the Premier League and Carabao Cup, with manager Xabi Alonso aiming to keep the team moving in the right direction throughout the 2026/2027 season.

According to BBC Sport on Saturday, 17 October 2026, the West London club faces a challenging schedule that includes important matches against Tottenham Hotspur, Liverpool and Manchester United.

The Blues will be eager to continue their recent progress as they approach a series of demanding fixtures that could test their ability to maintain consistent performances.

This upcoming stretch will also allow Alonso to assess his squad's fitness levels, tactical organisation and ability to cope with a congested schedule while competing for domestic honours.

Their next assignment will be a London derby against Tottenham Hotspur at Stamford Bridge on Saturday, 24 October. Chelsea will welcome their rivals for a Premier League contest scheduled to start at 5:30 pm, hoping to make the most of playing in front of their home supporters.

Chelsea's attention will then turn to the Carabao Cup, as they travel to Anfield to meet Liverpool in the competition's fourth round on Wednesday, 28 October. The encounter is scheduled for an 8:00 pm kick-off.

Securing qualification for the next stage will be Alonso's main objective, but Chelsea must produce a strong performance to overcome the challenge of facing Liverpool away from home.

The Blues will have little time to recover before another major test, as Manchester United visit Stamford Bridge on Saturday, 31 October. The Premier League clash is scheduled to begin at 12:30 pm, just three days after the trip to Liverpool.

With such a short interval between matches, Alonso may need to make strategic changes to his starting lineup to keep his players fresh and reduce the risk of fatigue.

Chelsea's next league match away from home will see them travel to Sunderland's Stadium of Light on Sunday, 8 November. The game will kick off at 2:00 pm, and the Blues will be targeting a strong performance to preserve their positive momentum on the road.

After the November international break, Chelsea will resume their Premier League campaign with a home fixture against Leeds United on Saturday, 21 November. The match is scheduled to start at 3:00 pm at Stamford Bridge.

These five matches could have a considerable impact on Chelsea's campaign, as Alonso faces the challenge of balancing tactical preparation, player fitness and squad rotation against several competitive opponents.

Chelsea's next five fixtures:

Chelsea vs Tottenham Hotspur — 24 October

Liverpool vs Chelsea — 28 October (Carabao Cup)

Chelsea vs Manchester United — 31 October

Sunderland vs Chelsea — 8 November

Chelsea vs Leeds United — 21 November