Chelsea's five best January transfers of all time

Cameron Smith

• Updated: 23 Jan 2025 09:34 CST
• 4 min read

Chelsea have signed some incredible players over the years, with the Blues consistently challenging for major honours over the past few decades.

While the bulk of their transfer business has been conducted during the summer window, a number of impressive signings have arrived at Stamford Bridge in January.

Below, FootballTransfers runs through Chelsea’s five best January transfers of all time.

READ MORE: Chelsea's five most expensive January transfers of all time

Tore Andre Flo - €450k (from SK Brann, 1998)

Tore Andre Flo is one of the best bargain signings in football history, with Chelsea paying just €450,000 to sign him from SK Brann back in 1998.

The Norwegian scored 50 goals in 163 appearances across a prolific 18-month stint at Stamford Bridge, and eight of those goals came during Chelsea’s debut Champions League campaign in 1999-2000.

Flo was eventually sold to Rangers for €18 million in 2000, having won five trophies during his time with the Blues, including the Cup Winners’ Cup and the FA Cup.

READ MORE: Chelsea's five worst January transfers of all time

Nicolas Anelka - €18m (from Bolton, 2008)

Nicolas Anelka was the epitome of a journeyman, but his most prolonged spell at a single club came during his time at Chelsea.

The Frenchman joined the Blues for €18m in 2008 and he quickly formed an immense strike partnership with Didier Drogba. Anelka won the Premier League Golden Boot in his first full season at Stamford Bridge, while he played a key role as the club won the Premier League and FA Cup double in 2010.

He did miss the crucial penalty during Chelsea’s shootout defeat to Manchester United in the 2008 Champions League final, but his overall spell with the Blues was extremely impressive.

Branislav Ivanovic - €12m (from Lokomotiv Moscow, 2008)

Branislav Ivanovic will go down as one of Chelsea’s best ever signings and he cost a mere €12m in January 2008.

The Serbian defender was plucked from relative obscurity and he went on to make 377 appearances for the Blues across a hugely successful nine-year spell with the club.

Ivanovic helped Chelsea win 10 trophies during his time at Stamford Bridge, including the Champions League, and he established himself as a Premier League great in the process.

Gary Cahill - €8.4m (from Bolton, 2012)

Arsenal, Manchester City and Tottenham Hotspur all wanted to sign Gary Cahill during his spell at Bolton Wanderers, but Chelsea won the race for his signature in January 2012 and he was an instant hit in west London.

Cahill played a pivotal role as Chelsea beat Bayern Munich in the Champions League final just six months after his arrival, while his partnership with John Terry was one of the best in the Premier League for several seasons.

The ex-England international racked up 290 appearances for Chelsea, winning eight trophies, before departing to join Crystal Palace in 2019.

Nemanja Matic - €25m (from Benfica, 2014)

Nemanja Matic’s first spell at Chelsea saw him fail to break into the starting XI, but the club opted to activate their buy-back clause following a string of sensational performances at Benfica, and that decision was inspired.

Matic immediately hit the ground running after his return to Stamford Bridge and was soon regarded as one of Europe’s very best midfielders.

The Serbian played a key role as Chelsea won the Premier League title in both 2014-15 and 2016-17, and the Blues even turned a nice profit when they sold him to Man Utd for just shy of €45m.