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Since Roman Abramovic’s takeover in 2003, Chelsea have won five Premier League titles. They have firmly established themselves as one of the biggest teams in Europe and have an enviable fanbase.
Given Chelsea’s current good fortunes, it is hard to believe they had to wait for 50 years to end their Premier League drought. In the 50-year stretch between 1955 and 2005, many great players tried to turn the tide, but ultimately went home empty-handed.
We will take a look today at the Chelsea stars who did their best but came up short.
Here are the top five Chelsea players who could not win the Premier League with the Blues:
#5 Frank Sinclair
Chelsea have had many colorful characters on their payroll over the years, but very few can hold a candle to the ever-energetic Frank Sinclair. The Jamaican joined Chelsea when he was only 11 years old and earned his first professional contract in 1990.
Chelsea manager Bobby Campbell handed the natural centre-back his debut in 1991, but on the left side of the pitch. He still managed to impress his coach and went on to make four more appearances in the 1990-91 season.
Sinclair was not a physically imposing defender, but had plenty of pace and energy to make up for it. He was also an exceptional motivator on the pitch, never failing to regroup his teammates during a difficult match.
Sinclair’s commitment allowed him to regain his place in the team time and again, even after long layoffs due to injuries or suspensions.
He failed to win the league title with the Blues, but won the FA Cup in 96-97, 1997-98 League Cup, and UEFA Cup Winners’ Cup.
#4 Steve Clarke
Steve Clarke, the manager who led Scotland to UEFA Euro 2020, their first major tournament in 23 years, used to don Chelsea’s colors.
The Scotland international moved to West London from St. Mirren in 1987 for €1million. His expertise as a right-back was well documented by then and he wasted no time settling down at Chelsea.
Clarke was not always the quickest off the block, but he more than made up for it with his game reading skills and passing ability. The natural right-back could also play on the opposite flank and even as a central defender, which made him one of the more valuable contributors.
Clarke won the 1997 FA Cup, 1998 Football League Cup and 1998 UEFA Cup Winners' Cup with Chelsea, but the league title eluded him.
For his remarkable 11-year spell at Chelsea, the right-back was included in Chelsea's centenary XI in 2005.
#3 Ruud Gullit
Chelsea bagged the signature of the great Ruud Gullit in July 1995, hoping to bring prestigious trophies to Stamford Bridge. Although at the twilight of his career, the Dutchman came with a big reputation.
He had won three Serie A crowns with AC Milan and three Eredivisie titles (two with PSV Eindhoven and one with Feyenoord), and even lifted the European Championship with the Netherlands in 1988.
At Chelsea, he adapted really quickly and was crowned the 1996 Chelsea Player of the Year. Thanks to his "Total Football" DNA, the natural second striker excelled in the middle of the park as well, regularly contributing with defence-piercing passes.
Unfortunately, even with his quality, Chelsea could not win the coveted Premier League title. Failing to win even a single trophy with the London outfit, Gullit first became the club’s player-manager in the summer of 1996 before retiring in 1998.
#2 Marcel Desailly
Back in the day, defenders generally had a one-track mind. Chelsea star Marcel Desailly was a shining exception to that rule. Desailly not only excelled as a centre-back but he was also a potent defensive midfielder and a sweeper.
Chelsea, however, mostly used his talents at the heart of defense, but having his versatility surely helped.
Desailly joined Chelsea from AC Milan in the summer of 1998. He went on to win the World Cup with France the same year, greatly increasing the expectations of Chelsea fans.
Fortunately, Desailly was not one to disappoint his supporters. He performed diligently for the London side for six straight seasons, featuring in 218 games.
The 2000 Euro Cup winner helped the club to the 1999–00 FA Cup and 1998 Super Cup, but could not bag the prestigious Premier League.
#1 Gianfranco Zola
Over the years, Chelsea have seen some exceptional performers weave their magic on the hallowed pitch at Stamford Bridge. They have dribbled, scored, and defended the crest with all their might, etching their name in the history books.
Gianfranco Zola, despite not winning a Premier League title with the Blues, is right up there with the very best. He is rated as one of the best players in the history of the great football club.
Zola moved to west London in 1996 and stayed put for seven long seasons. The two-time Chelsea Player of the Year was an exceptional dribbler and scored goals worth writing home about. The Italian won the FA Cup in his debut season and then another in the 1999-00 season.
He also won a League Cup, UEFA Cup Winners’ Cup, and the Super Cup with Chelsea, but could not manage to win the top-flight title.
He played 301 competitive games for Chelsea, scoring 75 goals.
