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#4 Danny Drinkwater
Very few people had praised Danny Drinkwater for Leicester City's Premier League triumph in 2016, yet Chelsea opted to reunite him with Kante anyway, signing him for £35 million in the summer of 2017. But things have not gone according to plan for the former Leicester man. The player has gone on to make just 30 appearances for the club since his arrival.
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He didn't play a single minute of Premier League football under Maurizio Sarri in 2018/19, with his only appearance coming in the Community Shield.
The midfielder was subsequently loaned out to Burnley (one hour on the pitch and one injury after a nightclub fight) and Aston Villa (four appearances and one disciplinary action after headbutting a teammate) in the 2019/20 campaign.
He was sent out on loan again to Turkish side Kasimpasa during the January transfer window, where he made 11 appearances before returning to the club this summer.
Chelsea are now looking to offload the midfielder permanently but it will be difficult to find suitors for a player who has barely played any football in the last three years.
#3 Tiemoue Bakayoko
Chelsea completed the signing of Tiemoue Bakayoko from Monaco in 2017, for a deal worth £40 million. The midfielder arrived with a big reputation after being part of a Monaco side who won Ligue 1 ahead of cash-rich PSG.
But the midfielder failed to impress during his 43 games for the club, earning criticism from fans and pundits for his performances in a Chelsea shirt.
The £40 million signing looked decent at times, especially when asked to attack the box from deep, but he never lived up to his billing as a top holding player who would strengthen the Blues' backline.
The midfielder has had loan spells at AC Milan, Monaco and Napoli and has been put up for sale this summer, having managed to play just one full season at Stamford Bridge.
#2 Fernando Torres
Chelsea's signing of Fernando Torres is one of those deals that is now associated with deadline day transfers.
The Blues signed the striker from Liverpool in January 2011 for a then-British record fee of £50 million. Torres was a goal-scoring machine for the Reds but that all changed when he arrived at Stamford Bridge.
He scored just 45 goals in 172 appearances for Chelsea, with a total of eight Premier League goals in the 2012/13 season being his best return in a single campaign.
The forward went on loan to AC Milan and Atletico Madrid before being sold to the latter in 2016.
Although he was not brilliant for Chelsea, fans are likely to remember his crucial goal against Barcelona in the semi-finals of their Champions League winning campaign in 2012.
#1 Alvaro Morata
Chelsea broke their transfer record in 2017 to bring Alvaro Morata from Real Madrid for a fee of £60 million. He was supposed to be a perfect fit for Chelsea, having shown glimpses of his talent at both Real Madrid and Juventus. But the striker failed to properly settle at Stamford Bridge.
Morata scored 11 goals in 31 appearances in his first Premier League season, but was in and out of the team for the first half of 2018-19. He was eventually loaned out to Atletico Madrid in the second half of the season.
The loan deal was made permanent by Atletico in the summer of 2019 and Morata has since openly admitted how he didn't enjoy his short time at Stamford Bridge.
