Chelsea had a great end to the 2024/25 season as they lifted the FIFA Club World Cup trophy by defeating Paris Saint-Germain in the final.
The Blues ranked fourth in the Premier League last season while also claiming the UEFA Conference League title.
Chelsea have quite a haul of new transfers in the summer window in accordance with their pattern of building an efficient squad of young talents.
While Enzo Maresca’s squad will be looking to add to their collection of silverware in the 2025/26 campaign, there could be some significant fixtures that affect Chelsea’s odds.
The Sporting News takes a look at the five league fixtures that could define Chelsea’s upcoming league season.
Manchester United (Away) – September 20, 2025
Chelsea are set to make the trip to Old Trafford to face Manchester United in the Premier League on September 20.
📲 Follow The Sporting News on WhatsApp
The Blues do not have a good record at Man United’s home ground, with only six wins in 33 league matches in comparison to the Red Devils’ 13 victories.
Maresca and his squad will be looking to bag a win against Man United to get their points up in the league table early on in the campaign.
Tottenham Hotspur (Away) – November 01, 2025
Chelsea’s first London derby of the upcoming season is against Tottenham Hotspur on November 1.
Spurs will be hosting the Blues at their home ground, where Chelsea have had quite some luck with claiming victories, bagging 16 wins in 33 matches.
Tottenham have only secured seven league wins against Chelsea at home. However, a London derby is always a charged affair, and the Blues will be hoping to leave the pitch with a victory in their hands.
Manchester City (Away) – January 03, 2026
Chelsea and Manchester City are neck to neck when it comes to their respective victories at the Etihad Stadium.
The Blues have won 13 out of 28 league matches at City’s home ground, while the hosts have secured 12 wins, with the remaining three games ending in a draw.
Chelsea are set to face Man City on January 3, 2026, at the Etihad, and the Blues will be attempting to maintain their lead in victories there.
Arsenal (Away) – February 28, 2026
The North-West London derby is undoubtedly among the matches that everyone looks forward to each campaign.
Along with the pressure of the historical rivalry, Chelsea have more to worry about in their upcoming Premier League match against Arsenal on February 28, 2026, at the Emirates Stadium.
Chelsea have an underwhelming record against Arsenal in the league matches held at the Emirates. The Blues have been on the receiving end of victory in only seven games in comparison to the Gunners’ 17 wins in 33 fixtures.
Arsenal have also been runners-up in the Premier League for three consecutive seasons now and will be chasing hard to claim the title in the upcoming campaign, making it a crucial match for both the Gunners and Chelsea.
Liverpool (Away) – May 09, 2026
Liverpool claimed the Premier League title last season and have been active in the summer transfer window to further bolster their squad for the upcoming campaign.
While the Reds will be coming to defend their crown in the 2025/26 season, Chelsea have quite a task at hand in their trip to Anfield to face Liverpool on May 9, next year.
Anfield has always been a tough ground for opponents, and the Blues have been no exception, with only seven wins in 33 league matches held at Liverpool’s home ground.
Chelsea’s away game against Liverpool in the Premier League is slated towards the end of the upcoming campaign, making it a crucial game for both sides with regard to their respective standings in the table at that point.
Chelsea news and related links
