Chelsea have a bad habit of firing managers, a lot of them, they’ve had 20 managers in 36 years! That means that Chelsea managers typically are on the job for less than two years. That’s crazy! To put in perspective, Liverpool have had 8 managers in those same 36 years.
The years 1990 to 1997 were a dark time for Chelsea. They went through five managers including Ian Porterfield and Glenn Hoddle and they won only two trophies.
In 1998 Gianluca Vialli joined the club and guided the Blues to five trophies. However, in 2000 the Chelsea boss lost his job after a bad start to the season.
Next came The Chosen One, Jose Mourinho. For seven years, Mourinho, the longest surviving Chelsea managers of the 21st century, guided the Blues to seven trophies including an EPL title. He left after power struggles after claiming the most trophies of any Chelsea manager.
After Mourinho came marching in a who’s who of European football managers…Grant, Scolari, Ancelotti, Conte, Hiddink, Sarri, Lampard, Tuchel, Potter, Pochettino, and finally, Enzo Maresca. That’s right, an astounding 11 managers in all between 2007 and 2025.
Then, in January 2026, Maresca left his job via board troubles and he had just beaten European champions PSG 3-0 in the Club World Cup final. These managers were amazing; they had a combined total of 12 trophies for Chelsea but the crazy thing is they were only there for 8 years and 4 months! And it affects their placing, the high reputation the club finished fourth last season but since their last manager change they dropped to sixth.
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As a Premier League fan I’ve seen managers come and go and it’s usually the smaller clubs that sell and buy managers but Chelsea as a top half side do it much more than the relegation battle teams. But to fully understand Chelsea’s incompetence of keeping managers we have to go back through all of the reasons Chelsea left their bosses.
Our story begins in 1988 when Chelsea appointed manager Bobby Cambell who joined from Portsmouth and had one major trophy to his name. At Chelsea he won two more and Chelsea could have entered a trophy winning era but no, in 1991, Chelsea had a poor run of results. Instead of trusting their manager, they just sacked him and brushed him aside like he was nothing.
Like many rash decisions, this one too came back to bite Chelsea. Their next manager; Ian Porterfield, was handed the task of tackling the newly formed Premier League but couldn’t handle it and was sacked after some bad results. Chelsea had fired a second manager and this time couldn’t replace him so they had to settle for an intern instead. So it was agreed that David Webb would see out the rest of the season.
Their next manager was Glenn Hoodle. He stayed at Chelsea for a good 3 years and saw out the dark age before moving on to the England national team. But Hoodle didn’t break the drought; that was accomplished by Ruud Guilt. In 1997 Ruud Guilt and Chelsea won their first trophy in six years winning 2-0 v Midsborough in the final. But Chelsea, being Chelsea, didn’t give Guilt a chance to win another, firing him in 1998.
Then Chelsea put their first phenomenon, Gianluca Vialli, in charge. Vialli actually played for Chelsea at the time he was appointed, and while juggling playing and managing, Vialli won 5 trophies and a treble in 1998. But when transfer disputes arose, Vialli was out.
The next manager was Claudio Ranieri. Ranieri was probably the longest manager to manage for Chelsea, win no trophies for them, and not get sacked after 18 months but Ranieri is virtually unknown. Why? He was overshadowed by his successor, Jose Mourinho.
There is no more known or popular name at Chelsea than Jose Mourinho. He won 6 trophies and had probably the best Chelsea squad the club had ever seen. He had players like Petr Čech, John Terry, Ricardo Carvalho, Clayde Makelele, Frank Lampard, and Didier Drogba. He won 2 Premier League titles, 1 FA cup, 2 League Cups, and a Community Shield. He was the stuff of dreams and utter legends. Yet, that wasn’t good enough for Chelsea as Chelsea let him go after only three years!
The next two seasons produced three managers (Avram Grant, Luiz Felipe Scolari, Guus Hiddick) and one FA cup. For clubs like Leeds, or West Ham an FA cup would be a dream come true, but not for Chelsea so Guus Hiddick was sacked and Carlo Ancelotti was signed
Carlo Ancelotti’s two year reign at Chelsea started with a Community Shield win. Then he went on to win two more trophies the next year. But like many others before him he was sacked, because 2011 was “under expectations” and the Real Madrid legend left the equation.
Then came a series of Chelsea managerial changes that each lasted around 2 years. First came Andre Villa-Boas with zero trophies then Roberto di Matteo with two trophies. After there was Rafel Benitez who won the Europa League, afterwards Jose Mourinho came back again and won them two trophies then Guus Hidick came and went as an intern. After that Antonio Conte and Mauzirizo Sarri won three trophies together.
Finally, someone came into Chelsea that all the fans were excited for: Frank Lampard. Lampard was one of Chelsea’s greatest midfielders, leading the Blues to multiple trophies for seven years before leaving for Manchester City, so, as you could imagine, the fans were happy to have him back. Unfortunately, as a Chelsea manager, he didn’t find success immediately in the form of trophies. Consequently, the club’s form deteriorated as he went on and, as is Chelsea’s way, he was soon sacked mid-season.
The replacement was the now England manager Thomas Tuchel who came in and won the Champions League, the Super Cup, and the Club World Cup. And he probably would have continued winning if Roman Avorvitch, the then Chelsea owner, didn’t ruin it. He sold the club and the new owners immediately sacked Tuchel and signed the infamous Graham Potter, the man who almost drove west ham to relegation in the 2024-2025 season and is the reason they got relegated this season. And he didn’t do much better at Chelsea with atrocious league form, and he was sacked after seven months and ‘Super Frank’ came back in to finish the season.
The 2023-24 season was an interesting season for Chelsea’s their new manager Mauricio Pochettino. Pochettino had come to them from the French powerhouse Paris Saint-Germain and after winning three trophies with PSG including Ligue I, he was ready to get Chelsea back to winning ways. The start of the season looked promising for Chelsea with the emergence of their new superstar Cole Palmer, but it was not to be. Chelsea finished 6th, trophyless, and without European qualification, so Pochettino was quickly sacked.
At the end of the Pochettino era Chelsea were left trophyless two years in a row and in the lowest European competition. They needed at least Champions league qualification or one trophy so decided to try something new: a manager on the rise. Chelsea went with Enzo Maresca, a manager that went from the Serie B to the Championship and was about to start his second season with Leicester City in the Prem after getting them promoted last season. He was too good to be true, exactly what Chelsea needed, so Chelsea scooped him up.
As soon as Enzo Maresca started at Chelsea there was something different about the club, they attacked with a little more intensity, they defended with a little more passion, and their midfield was a little bit stronger. Their first few games showed it winning 6-2 against Wolves, drawing 1-1 with the then strong Palace, and then winning again 1-0 against Bournemouth. Chelsea had an amazing season, they finished 4th, gained the champions league for the next season, and won the conference league and club world cup.
This season was set up to be great, too, but Maresca left by mutual consent in January after getting an offer from Man City to replace Pep at the end of the season and after falling out with some of the club staff it seemed right to leave. Chelsea needed a new manager and fast, so that’s when they appointed their last temporary manager of the season: Liam Rosiner. Rosiner was an extremely surprising choice. He was young and inexperienced. In addition, he also had never coached for a big club before (his former clubs being Hull City and RC Strasbourg) and he was really not a favorite to do well. And most people were right; he was an absolute disaster with Chelsea going on a 5 game goalless losing run BlueCo sacked on the spot and hired an interim manager to finish out the season.
Now, for the 26-27 season it’s Xabi Alonso’s turn to face the wrath of the Chelsea board. Maybe he is what they need, maybe he is good enough for them, but if I were him I wouldn’t get too comfortable because if we know one thing about the Chelsea board it is that they don’t care whether or not you’re a tactical genius or you’ve won the Champions League two times in a row they’ll treat you the same; give 18 months or less to make them the best team in the world and if you don’t you can say goodbye to Stanford Bridge. So, best wishes from this writer to Xabi Alonso because it doesn’t matter who you are or where you come from, it only matters that you get them trophies.