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#3 Chris Sutton - £13.5 million
One of the big names to arrive at Chelsea before the Abramovich era, Chris Sutton's career never really took off at Stamford Bridge.
Signing from Blackburn Rovers for a then club-record £13.5 million in 1999, Sutton was considered the player that would help the Blues challenge for the Premier League title. The striker scored 50 goals in 131 games for Blackburn and had also won the 1994-95 Premier League title with the club.
However, Sutton managed to score just two goals in 38 appearances across all competitions for the Blues and looked a complete shadow of his former self.
As such, when Celtic came in with a offer of £9 million in the following season, the Blues gladly accepted it and the striker moved to Scotland. He had an impressive spell with the Scottish club, scoring 63 goals in 130 games, winning four Scottish Championships, three Scottish Cups and one Scottish League Cup.
Sutton returned to England playing for the likes of Birmingham City and Aston Villa before hanging up his boots in 2007. He now works as a pundit and commentator for BBC Sports.
#2 Frank Lampard - £14.4 million
Arguably Chelsea's greatest ever signing, Frank Lampard, has won everything there is to win at Stamford Bridge and is a club legend.
Although he was a key part of Roman Abramovich's era at Chelsea, Frank Lampard arrived at the club before the Russian's takeover. The midfielder was signed from West Ham for £14.4 million in 2001, a pretty expensive transfer considering the club's finances at the time.
Having been backed by Harry Redknapp, who said Lampard "will go right to the very top" in a famous interview, the midfielder has proved that statement right during his time at the Blues.
He's the club's record goalscorer, despite being a midfielder with 211 goals and is fourth on the all-time list of appearances for the Blues with 648. The midfielder is third on the all-time list for Premier League appearances with 609. He is fifth for all-time goals in the league with 177 and fourth for assists with 102.
He has won 13 pieces of silverware for the Blues, including three Premier League titles, one Champions League and one Europa League. He also finished as the runner-up for the 2005 Ballon d'Or while winning the FWA Footballer of the Year award during the same year.
Lampard did return to manage his beloved club, although his managerial stint wasn't quite as successful.
Nevertheless, Lampard is a Chelsea legend and considering he was signed for just £14.4 million, the deal was an absolute steal.
#1 Jimmy Floyd Hasselbaink - £20.25 million
And finally, the most expensive signing before the Abramovich era was none other than Dutch international striker Jimmy Floyd Hasselbaink. The forward moved to Stamford Bridge in 2000 from Atletico Madrid for a fee of approximately £20 million.
Hasselbaink already had the experience of playing in the Premier League, having spent two seasons with Leeds United during which he won his first Premier League Golden Boot.
At Chelsea, Hasselbaink was a prolific goalscorer, especially during his first two seasons at the club. He made 177 appearances in all competitions for the Blues and registered 87 goals and 25 assists during that time. He even managed to win his second golden boot after scoring 23 goals in his first season for the Blues.
Hasslebaink departed from Chelsea in 2004, and went on to play for Middlesbrough, Charlton and Cardiff before retiring in 2008. He is currently the manager of Burton Albion in League 1.
