Under Roman Abramovich, silverware at Chelsea felt like an expectation, but new ownership has instead seen the Blues chasing Champions League football in crucial games.
Chelsea fans will always reminisce about the glory years under Abramovich with countless trophies, European triumphs and a squad built on world-class talent. But since his departure and Todd Boehly’s high-spending takeover, the identity of the club has been anything but stable.
With just one major trophy lifted since the Russian billionaire left, and a chaotic rebuild still unfolding, this new Chelsea has been built on matches that have directed the project.
10. Chelsea vs Newcastle – March 2024
Nicolas Jackson got things going early in the game, but Chelsea’s lead didn’t last as Isak hit back before the break. Cole Palmer and Mykhailo Mudryk both scored, giving the Blues some breathing room before Murphy tried to close the gap.
At the time, Chelsea were stuck in 11th with just 10 league wins all season. But this match felt like a turning point. They went on to bag 24 points from their final fixtures, just missing out on the Champions League.
Sixth place wasn’t the goal, but it paved the way for Chelsea to win the Conference League.
9. Chelsea vs Everton – April 2025
Nicolas Jackson ended his 15-game goal drought with a first-half strike against Merseyside club Everton. The 1-0 win orchestrated by the Senegalese striker pushed Chelsea into the top four keeping European dreams alive.
Head coach Enzo Maresca watched on from the stands following his suspension after his third card of the season against West London neighbours Fulham.
8. Tottenham vs Chelsea – December 2024
You don’t forget games like this. Chelsea went down 2–0 within 15 minutes but didn’t look defeated. Manchester United loanee Jadon Sancho got the ball rolling for the Blues and clawed a goal back, but then it turned into the Cole Palmer show.
Two penalties from the standout former Manchester City youngster put Chelsea ahead in the second half. Enzo Fernández got in on the action too as Chelsea flipped the script and left Spurs stunned.
A rollercoaster of a game, but one that sparked serious belief in the squad. This wasn’t just a derby win, it was a statement.
7. Fulham vs Chelsea – April 2025
Chelsea pulled off a dramatic comeback at Craven Cottage after falling behind in the first half. The equaliser came from academy star Tyrique George, who notched his first Premier League goal and staked a serious claim for more first-team minutes.
Pedro Neto then grabbed a stoppage-time winner, sealing three points in one of the most emotionally charged derbies of the season.
George’s breakout moment proved pivotal—he went on to score again in the 3–0 Conference League quarter-final win over Legia Warsaw, showing the kind of impact Chelsea’s rebuild is starting to deliver.
6. Chelsea vs Liverpool – May 2025
Chelsea stunned newly-crowned champions Liverpool with a ruthless performance at Stamford Bridge. Early strikes from Enzo Fernández and a Jarell Quansah own goal put the Blues firmly in control, and Cole Palmer added a late penalty to wrap things up.
The result reignited belief in the dressing room and gave fans a glimpse of what the team could do under pressure. It also boosted Chelsea’s late-season charge for a European spot, proving they could still challenge the best.
5. Burnley vs Chelsea – October 2023
Chelsea thrashed Burnley 4-1 away, but it was Palmer’s performance that stood out most, scoring his first goal for the club. This game marked the real beginning of Palmer’s rise.
The winger not only got on the scoresheet but also played a pivotal role in linking up with Sterling and Jackson, giving the Blues a much-needed attacking edge. It was the match that signalled Palmer’s emergence as a key figure in Chelsea’s evolving rebuild.
4. Chelsea vs Manchester United – May 2025
A big game with even bigger stakes. Chelsea knew anything less than a win would hand the top-four advantage back to Villa, but Marc Cucurella stepped up with a thumping header to seal the deal.
United had the Europa League final on their minds, but Chelsea dominated with seven shots to United’s four and a dominant midfield display. It wasn’t a fixture that will go down in history books, but it kept Chelsea with hopes of the highest level of European football.
3. Nottingham Forest vs Chelsea- May 2025
Final day drama with Chelsea needing three points, and a little help elsewhere, to clinch a Champions League return. Newcastle and Aston Villa both did the Blues a favour by losing their respective matches, but it would’ve meant nothing without Levi Colwill’s second-half header.
The win confirmed a fourth-place finish, Chelsea’s best league position in three seasons. In a year full of setbacks, this was a big step back to the club’s former expectations.
2. Chelsea vs Manchester City – November 2023
One of the most exciting Premier League matches in recent memory, Chelsea’s 4–4 draw with Manchester City at Stamford Bridge was pure drama from start to finish.
The game saw five lead changes, with goals from six players and a 95th-minute penalty from Cole Palmer, scored against his former club, to salvage a point.
This wasn’t just a thrilling watch, it was a genuine turning point for the Blues. After weeks of underwhelming form, Chelsea matched the reigning champions blow for blow.
1. Real Betis vs Chelsea – May 2025
After trailing at half-time and looking to be struggling to contain Real Betis’ constant attacks on goal, Chelsea mounted a remarkable comeback with goals from Enzo Fernández, Nicolas Jackson, Jadon Sancho, and Moisés Caicedo.
The victory secured their first UEFA Conference League title and completed their collection of all major European trophies. The win was Chelsea’s first trophy under Todd Boehly’s ownership and their first piece of major silverware since they won the Champions League in 2021.
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