The Blues have found new life this season after horrific recent seasons. The arrival of the new coach along with the new additions and emergence of Cole Palmer in the midfield have created a new wave. Although the Club has struggled for a couple of years now with ownership and managerial crisis, there were times when the club had the most successful football managers in Chelsea history.
From Mourinho’s double reign to Ancelotti’s tactics, there is a rich history in the touchline of Stamford Bridge. The Chelsea managers have taken the club to many silverware over the past decades.
Established in 1905, the Club quickly made a name for itself with the highlights of Blue Kits and a passionate fanbase. However, after the arrival of Roman Abramovic, the club reached new heights and started getting their popularity worldwide. The Special One’s arrival at the club had marked a new era. With him came back-to-back Premier League titles. The club won their first Champions League title under the short tenure of Roberto Di Matteo. The history repeated back again with Tuchel when they beat Man City in the finals in 2021.
Safe to say, Chelsea’s history is filled with many great managers. In this post, we will take a look at the best Chelsea managers as per the most wins in the history of the club.
Table of Top 10 Chelsea Managers With Most Wins in the Club History
| Manager | Wins |
| David Calderhead | 384 |
| Jose Mourinho | 204 |
| Ted Drake | 148 |
| Dave Sexton | 142 |
| Tommy Docherty | 117 |
| Claudio Ranieri | 107 |
| Gianluca Vialli | 83 |
| Antonio Conte | 69 |
| Carlo Ancelotti | 67 |
| Thomas Tuchel | 60 |
10. Thomas Tuchel- 60 wins
The German manager is known for his aggressive attacking strategies. Came in the Club when it was going through ownership changes. He handled the club beautifully after Frank Lampard established the philosophy within the team.
Together the team went on to win the Champions League that year, defeating Manchester City in a 1-0 match and clinching the second UEFA Champions League trophy for the club. In his 100 matches he had won 60 of them.
| Manager | Matches | Wins | Win rate |
| Thomas Tuchel | 100 | 60 | 60% |
9. Carlo Ancelotti- 67 Wins
Up next we have the Italian manager who is now the manager of Real Madrid. In his tenure, he managed 109 matches, winning 67 of them.
Don Carlo has led the Blues to win not only the Premier League but the FA Cup as well. Truly the Italian manager has had success in every club league.
| Manager | Matches | Wins | Win rate |
| Carlo Ancelotti | 109 | 67 | 61.46% |
8. Antonio Conte- 69 Wins
The Italian arrived in the Premier League in 2016 with big baggage of expectations and a big task to rejuvenate Chelsea after a poor 2015/16 season. In his tenure of 2016-2018, the Italian had won 69 matches as the Chelsea manager. Conte is known for demanding the best out of his players and he got the best of players like Diego Costa and Kante that time instantly.
The Chelsea manager led the club to League glory in 2016-17 as the Blues won the Premier League title with a record of 13-game winning streak. Moreover, he also won the FA Cup. The tactical 3-4-3 was a nightmare for many teams.
| Manager | Matches | Win | Win Rate |
| Antonio Conte | 106 | 69 | 65.1% |
7. Gianluca Vialli- 76 Wins
Up next, we have Gianluca Vialli. He was the Chelsea manager from 1998 to 2000. During his tenure, he won multiple trophies. Among them, he has clinched the trophies of the UEFA Cup Winner’s Cup and League Cup. Under his reign, Chelsea was a nightmare both in the League and European competition.
| Manager | Matches | Wins | Win Rate |
| Gianluca Vialli | 143 | 76 | 53.2% |
Also Read: 5 Worst Chelsea Managers Ever in Club History | Ranked
6. Claudio Ranieri- 107 Wins
From 2000 to 2004, the manager won 107 games as the Chelsea manager. He had developed a great squad which qualified for the Champions League. They also reached the semi-finals multiple times. He had pretty much laid out the groundwork for the success that was followed under the Special One.
| Manager | Matches | Wins | Win Rate |
| Claudio Ranieri | 199 | 107 | 53.8% |
5. Tommy Docherty- 117 Wins
From 1961 to 1967 Docherty was the manager of Chelsea. Before him, the Club was in the second division. In his tenure at the club, he had won 117 games.
He pretty much revitalized Chelsea in the 1960s, obtaining promotion back to the First Division and reaching multiple semi-finals. The youth-focused approach made the team a competitive and vibrant side.
| Manager | Matches | Wins | Win Rate |
| Tommy Docherty | 240 | 117 | 48.75% |
4. Dave Sexton- 142 wins
With 142 wins, he is one of the best in terms of Chelsea managers win percentage. From 1967 to 1974, he was the manager of the Club. Fans know Sexton as the one who led the club to a few of their biggest successes in his tenure.
However, his most famous milestone was when he led the Club to win the 1970 FA CUP against Leeds. Following that year, he helped the Blues to be the winners of the 1971 UEFA Cup Winner’s Cup.
If we speak about his tactics, he had a unique approach of balanced strong defence with creativity up front when they were going forward.
| Manager | Matches | Wins | Win Rate |
| Dave Sexton | 253 | 142 | 56.1% |
3. Ted Drake- 148 wins
In his 1952 to 1961 tenure, Ted Drake won around 148 games as the Chelsea manager. He led the Club to their first-ever League title back in 1955. He is adored by the fans for his contributions to modernizing the club, eliminating removing the ‘Pensioners’ nickname and logo.
From branding to good league finishes, he is considered more than just a manager by the Chelsea fans.
| Manager | Matches | Wins | Win Rate |
| Ted Drake | 426 | 148 | 34.7% |
2. Jose Mourinho- 204 wins
The Special One had two tenures with the Club. Upon his arrival from Champions League Winner Porto, the manager made sure to let all the club know that he is the special one. And he backed up all his statements. Upon his arrival, he bought Drogba, and the rest is history.
In his two tenures of 2004-2007 and 2013-2015, the Portuguese have won 204 matches. If he talk about trophies, Mourinho had won three Premier League titles, two League Cups, and one FA Cup.
He had made sure the Club was a powerhouse in the League. From his touchline antics to his tactical approach to the game, he was the manager in the League that every other club dreaded to face. He was truly the Special One for the Club.
| Manager | Matches | Wins | Win Rate |
| Jose Mourinho | 321 | 204 | 63.6% |
1. David Calderhead- 384 wins
Calderhead was the manager of Chelsea for 26 years. His tenure was from 1907 to 1933. David had won a total of 384 games in his tenure in 966 games. Even though he did not win major trophies, his reign helped the Club establish itself in the top tier of English Football.
| Manager | Matches | Wins | Win Rate |
| David Calderhead | 966 | 384 | 39.8% |
Also Read: 15 Chelsea Managers from the Abramovich Era to Present Day
FAQ’s
Q. Who is the manager with the most wins in Chelsea history?
David Calderhead is the manager with the most wins in Chelsea’s history
Q. How many wins did Frank Lampard achieve as Chelsea’s manager?
Frankie had won 44 matches in his tenure as the Chelsea manager.
Q. Which manager ranks second in terms of most wins for Chelsea?
Jose Mourinho ranks second in terms of most wins for Chelsea.
Q. What was Carlo Ancelotti’s win record at Chelsea?
67 matches was Carlo Ancelotti’s win record at Chelsea.