Bet on Chelsea FC

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Chelsea. A club that always evokes reactions. Proud fans, passionate opponents. Whichever camp you put yourself in, one thing is certain: it is never boring. From the rivalry in London to challenging established names from Manchester and Liverpool… In the Premier League, betting on Chelsea always delivers interesting bets. Add to that the Champions League clashes and you know Chelsea are a club that irrevocably ends up on your betting sheet. We dive into the history of The Blues, past highlights and icons and, en passant, tell you how best to bet on Chelsea.

Love ’em or hate ’em, betting on Chelsea always yields interesting bets. Chelsea is always labelled by haters as a club with no history. But history doesn’t lie. Indeed, in 1905, a club of gentlemen raised £5,000 in shares of one pound each (if only you could have tried your hand at that) to found the professional football club Chelsea.

Chelsea was a typical club with ups and downs. Attracted top players from time to time, but never really played consistently in the upper echelons. For years, Chelsea found themselves back in the second or third division. Let’s cautiously say that betting on Chelsea was not as popular then as it is now.

Turning point for the club was the appointment of Ruud Gullit as manager-player.

The Dutchman managed to attract great players to the club, making it a regular in the Premier League. It even entered the Champions League for the first time in 1999. In the 2002-03 season, Chelsea qualified for preliminary rounds of the Champions League. In fine fashion too, by beating Liverpool on the final day of the season. A great day for Premier League Sports Betting that was. It was the match that ensured Abramovic bought the club and made it into the footballing elite it is today!

History of the club

So Chelsea’s founding date is 10 March 1905. However, the first step was taken as early as 1896. That was when businessman Gus Mears actually bought Stamford Bridge Athletics Ground to play football there. It was not until 1904 that this was possible and then he wanted to lease the stadium to Fulham. They refused and so a year later Chelsea was founded, named after the district next to Fulham.

Chelsea FC started in the Second Division in 1905. After just two seasons, the club promoted to the highest First Division. For the first few years, Chelsea was a yo-yo between First and Second Division. In 1915, the club fell short of a major prize when it lost the FA Cup final to Sheffield United. The club was known for attracting top players, though, and therefore often had the highest spectator numbers.

Modernisation and first Chelsea title in 1950s

Between the First and Second World Wars, Chelsea fared well. The club finished third in the First Division in 1920 and reached the FA Cup semi-finals in 1920 and 1932. In the 1930s, Chelsea was a regular in the top division, but mostly in the right-hand row. After World War II, that continued again, fluctuating between 13th and 20th place.

In 1952, Ted Drake joined as coach. In the 1930s, he had twice become national champion with Arsenal and five-time international for England. He improved youth training and the training regime, and brought in players from lower leagues. In 1954-1955, he crowned his work with the English national title. But at the insistence of the English league, Chelsea did not enter the new European Cup tournament organised the following year for European national champions.

First European prize Chelsea

After the national title, however, the club fell straight back into the right-hand row. Ted Drake was sacked in 1961 and succeeded by Tommy Docherty. He mainly brought in talented players from the youth. That went well, but unfortunately only one prize came out of it: the League Cup of 1965. Apart from that, several near-successes. In three seasons, Chelsea lost two FA Cup semi-finals and one final. It also lost the semi-final Inter-Cities Fairs Cup (predecessor UEFA Cup/Europa League) to FC Barcelona.

In 1967, Dave Sexton took over as Chelsea’s coach. That led to 1970 FA Cup wins and Chelsea were allowed to enter the European Cup Winners’ Cup. In the semi-final, they beat Manchester City (winner of the previous year) and in the final Real Madrid over two duels. Sexton also led the club to the (lost) 1972 League Cup final. Betting on Chelsea was sexy again under Sexton.

Financial problems, relegation and rebuilding

However, the 1970s also saw the start of financial problems for Chelsea, partly due to ambitious renovations of the Stamford Bridge stadium. The club was also plagued by many hooligans among its supporters – the notorious ‘Chelsea Headhunters’. Chelsea were relegated to the Second Division twice in the 1970s. In 1983, the club narrowly avoided relegation to the Third Division.

A year before, in 1982, businessman Ken Bates had acquired the club for the symbolic sum of £1 from Brian Mears (grandson of co-founder Joseph Mears, brother of Gus). In 1985 and 1986, Chelsea finished sixth in the First Division, but two years later they were relegated again – with direct promotion following. Incidentally, the club won the Full Members’ Cup twice during that time. An extra tournament for English clubs after five years of exclusion from European tournaments due to the 1985 Heysel drama.

More European prizes under Gianluca Vialli

In the mid-1990s, Chelsea again did reasonably well in the newly formed Premier League. In 1994, they still lost the FA Cup final to Manchester United. Three years later, Chelsea won the world’s oldest cup tournament under the leadership of player-trainer Ruud Gullit. By February 1998, however, Gullit was sacked in favour of his teammate Gianluca Vialli.

The Italian was extremely successful in 2.5 years at Chelsea. In 1998, he won A year later, Chelsea under Vialli also finished handsomely third in the Premier League and in 2000 won the FA Cup. Despite first qualifying for the Champions League (and quarter-finals therein), Vialli was sacked in September 2000, and in came Claudio Ranieri. However, betting on Chelsea was once again featured on many more bet slips.

Chelsea: Roman Abramovich and José Mourinho

In 2003, Chelsea again found themselves in financial dire straits. Ken Bates decided to sell the club to Russian businessman and billionaire Roman Abramovich. There were whispers that Vladimir Putin had ordered him to do it, to expand the Kremlin’s influence. However, Abramovich has always denied this, despite being good friends with Putin.

Abramovich took over much of the debt, but his most important action at Chelsea was to recruit José Mourinho as coach. The Portuguese had won the Champions League with FC Porto in 2004. He did not succeed at Chelsea, but he did win some great prizes. In 2005 and 2006 the Premier League, an FA Cup and twice the League Cup. In 2007, Mourinho was sacked and succeeded by Avram Grant. The Israeli led Chelsea to the Champions League final in 2008. However, Manchester United including Cristiano Ronaldo and Edwin van der Sar won on penalties.

Carlo Ancelotti and Roberto di Matteo: Premier League and Champions League

In 2009, Guus Hiddink was briefly “interim pope” at Chelsea, but did win the FA Cup en passant. He was succeeded by another success coach, Carlo Ancelotti. The Italian immediately won three prizes in his first season: Community Shield, Premier League and FA Cup. After a short spell of André Villas-Boas (June 2011 – March 2012), former player Roberto di Matteo was appointed coach.

The Italian received two awards practically in his lap. He won the FA Cup in his first two months and, with Chelsea, became the first London club to win the Champions League – after beating Bayern Munich in the final. Eight months after his appointment, however, Di Matteo was already back on the doorstep. Rafael Benitez provided Chelsea with a stunning performance in 2013.

By winning the Europa League, Chelsea were one of five clubs to have won all three pre-1999 European tournaments. The other four were Juventus, Ajax, Bayern Munich and Manchester United. Chelsea seemed to have permanently entered the absolute top of international football. Betting on Chelsea increased in popularity worldwide. After all, success attracts.

José Mourinho, Guus Hiddink, more Italians and Thomas Tuchel

In 2013, an old friend of Roman Abramovich returned, José Mourinho. The Portuguese led Chelsea to their fifth league title and a League Cup in his second season. However, he was allowed to leave early in 2015 after a poor start to the season. Guus Hiddink was allowed to try for six months, but it did not go well. His successor Antonio Conte won the 2017 Premier League and 2018 FA Cup. Subsequently, Maurizio Sarri grabbed the second Europa League with Chelsea in 2019.

His successor and club icon Frank Lampard won nothing in a year and a half and was replaced by Thomas Tuchel in January 2021. The German coach must have had a ‘Di Matteo feeling’, as four months later he won the Champions League with Chelsea. Later, he also picked up the World Cup for clubs and the European Super Cup. Just before that, in April 2011, Chelsea got into trouble with UEFA over the announced Super League. However, they quickly withdrew from that.

In March 2022, owner Roman Abramovich came under great pressure due to the Russian invasion of Ukraine. He eventually decided to sell the club in May 2022 to an investment group led by American Todd Boehly. Sportingly, another change came in September. After finishing third in the Premier League in 2021-2022, Tuchel was already out on the street and Graham Potter arrived.

Betting on Chelsea Managers?

The attentive reader has seen that Chelsea effortlessly put managers on the street, bring them back, put them back on the street, make successes from the not-so-distant past barely count… In short, betting on Chelsea managers is almost as normal as betting on matches of The Blues.

Rivals of Chelsea

London is a busy football city and therefore home to several rivalries. Traditionally, Chelsea, Arsenal and Tottenham Hotspur have been arch-rivals of each other. There is also a strong rivalry with Leeds United, following several heated duels in the 1960s and 1970s. Fans have also increasingly seen a rivalry with clubs like Manchester United and Liverpool in recent years. The latter club encountered them a lot in the FA Cup and League Cup in recent years.

Club icons Chelsea

There are three players who came to more than 700 games for Chelsea. Two of them played pretty much the entire 1960s and 1970s for the club: record holder Ron Harris (795 duels) and number two Peter Bonetti (729 duels). As such, they won the FA Cup in 1970 and the European Cup Winners’ Cup in 1971. John Hollins was also a strong player at the time, reaching 592 games (fifth all-time). Dave Sexton was the coach between 1967-1974. Bobby Tambling scored a whopping 202 goals in 370 games for Chelsea between 1959 and 1970. Peter Osgood accounted for 150 goals between 1964-1974.

In the second half of the 1990s, Chelsea were already successful in England and Europe. Gianluca Vialli won the most awards as coach during that time. Dennis Wise was one of the key players at the time, alongside later coach Roberto di Matteo, Graeme Le Saux, Marcel Desailly and Gianfranco Zola. Between 2000 and 2004, Oranje striker Jimmy Floyd Hasselbaink was a crowd favourite and goal scoring machine.

John Terry experienced a few more of those successes and would play for Chelsea from 1998-2017. With 717 games, he ranks third all-time, just ahead of generational rival Frank Lampard. From this strong squad, fans naturally also immediately spoon out the names of goalkeeper Petr Cech and top striker Didier Drogba. And of course, success coach José Mourinho cannot be forgotten.

Retrospective Chelsea season 2021/2022

Last season started well under coach Thomas Tuchel. He won the European Super Cup and the World Cup for clubs. In the Premier League, they were ‘best of the rest’ behind Manchester City and Liverpool. But two particular games will have hurt more. Chelsea lost its third FA Cup final in a row and the League Cup final, both to Liverpool. In the Champions League quarter-finals, the club lost to Real Madrid in extremis. For die-hard fans, betting on Chelsea thus led to tears more than once.

Outlook Chelsea season 2022/2023

In the Premier League, Chelsea could be back at the top, competing with Manchester City and Arsenal, as always. But new owner Todd Boehly will also set his sights on the Champions League. That should be without Timo Werner and Romelu Lukaku, but with new acquisitions Pierre-Emerick Aubameyang and Raheem Sterling. Much is also expected of new coach Graham Potter. Hopefully he will be given time by Boehly to prove himself at Chelsea.


  • How many trophies has Chelsea FC won in total?

    In total, Chelsea FC have won 36 trophies, including 8 FA Cups and 6 Premier League trophies. Chelsea FC was the first English football club to have won the three biggest UEFA trophies, namely the European Champion Clubs’ Cup, UEFA Europa League, and European Cup Winner’s Cup.

  • Where does Chelsea FC have the most fans?

    Jokingly, Chelsea have the most online fans in Nigeria, rather than England where the club hails from. Yet they are one of the most popular clubs in England, where they may have more fans than their rivals. Among famous Brits, the club counts actor Sir Michael Caine, director Guy Ritchie, presenter Jeremy Clarkson, and celebrity chef Gordon Ramsey as fans.

  • What is Chelsea FC’s nickname?

    The club is often referred to as “the Blues” because of their blue uniform. Over the years, the club has also received many nicknames from their rivals, often with reference to the club’s financial owners.

  • How many trophies has Chelsea FC won in total?

    In total, Chelsea FC have won 36 trophies, including 8 FA Cups and 6 Premier League trophies. Chelsea FC was the first English football club to have won the three biggest UEFA trophies, namely the European Champion Clubs’ Cup, UEFA Europa League, and European Cup Winner’s Cup.

  • What is the Chelsea Supporters’ Trust?

    The Chelsea Supporters’ Trust is an independent organization that represents the interests of Chelsea fans. It aims to enhance communication between the club and its supporters and to maintain the fan perspective in club matters.

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