Powered by Roundtable

Five critical matches loom. Chelsea battles for Premier League points and FA Cup glory, balancing ambition with a demanding schedule.

Chelsea begins an intense stage of the calendar with commitments combining league and cup. The team led by Liam Rosenior needs to consolidate results to climb positions in the Premier League and stay alive in the FA Cup, while managing efforts to tackle both fronts with a competitive squad. Next, here are its next five fixtures.

Wolverhampton Wanderers vs. Chelsea, Matchday 25 of the Premier League.

Chelsea will visit Wolves at Molineux to resume their fight to add points to the table. The immediate precedent between the two favors the Blues, who won 3-0 in the last league clash, although Molineux is usually an uncomfortable and demanding venue for big teams. The match will open the series of fixtures that will define the team's rhythm in the league.

Chelsea vs. Leeds United, Matchday 26 of the Premier League.

Back at Stamford Bridge, the Blues host Leeds United in a key duel to maintain consistency at home against direct rivals in the relegation battle. The last meeting between the two ended with a 3-1 victory for the home side.

Hull City vs. Chelsea, FA Cup 4th Round.

In the oldest cup competition in football, the Blues will visit Hull City, an interesting challenge as the rival plays in the lower tiers and will look to cause an upset. In the previous round, the Tigers secured qualification after beating Blackburn Rovers in a tight penalty shootout, following a draw in the match, while Chelsea sealed its passage with authority after a resounding 5-1 victory over Charlton, a result that reinforced its status as a contender in the tournament.

Chelsea vs. Burnley, Matchday 27 of the Premier League.

Back to the league, the Blues host Burnley at Stamford Bridge, in a duel where securing the three points will be key to climbing towards European spots. The immediate precedent between the two is favorable for Chelsea, which won 2-0 as the away side in the last meeting.

Arsenal vs. Chelsea, Matchday 28 of the Premier League.

After completing these next five fixtures, Chelsea once again faces Arsenal in the Premier League, a high-level clash of importance in the battle for the top positions in the table. Recent history between the two adds spice to the duel: the second leg of the EFL Cup semifinals was a 1-0 win for the Gunners (4-2 on aggregate), thus ending the Blues' run in the competition, while the last league clash, played 30 November 2025, ended 1-1, reflecting the parity that usually marks this London derby.

Chelsea is in a challenging phase of the calendar following its EFL Cup semifinal against Arsenal, with five matches that will define the course of its campaign between league and cup. From Molineux to Hull, the coming days will be demanding for the Blues, who seek to balance physical demands and results to maintain their aspirations in all competitions.

Join The Conversation

Roundtablesports is Free to join! You can post your own thoughts, comment on articles, and start conversations with our Roundtable Writers. Scroll up to the top of the page and click 'Join'.

Download the FREE Roundtable APP, and get even easier access to your favourite teams and news!

Topics:News