[11] On 31 August, transfer deadline day, Chelsea signed Saúl from Atlético Madrid on a season-long loan with an option to buy at the end of the season.

Chelsea's successful defensive performances led to Antonio Rüdiger being nominated for Premier League Player of the Month, though it was eventually awarded to Cristiano Ronaldo.

Chelsea rallied to win with two late goals from Timo Werner and Ben Chilwell, who scored with a close-range left-footed volley in his first start in the Premier League during the season.

Five minutes later, Thiago Silva cleared a shot from former Chelsea player Álvaro Morata off the line with a dramatic overhead kick to preserve the one-goal advantage at the break.

[59] Chelsea's third competitive defeat of the season came on December 4 as they travelled to the London Stadium to take on West Ham, who sat in fourth place in the Premier League.

[63] Five days later, Chelsea returned to action at Stamford Bridge without Timo Werner, Romelu Lukaku, and Mateo Kovačić due to COVID-19 against an injury-struck Everton.

[70] On 31 December, Sky Italia released an interview with Romelu Lukaku from earlier in the month in which the striker stated that he was unhappy with his lack of game time at Chelsea and eventually wished to return to former club Inter Milan.

Chelsea attacked frenetically before the interval, and in first-half stoppage time, Christian Pulisic controlled N'Golo Kanté's lofted pass and finished powerfully to level the score line at 2 goals for each side.

Chelsea won the match 2–0, courtesy of a goal from Kai Havertz and a Ben Davies own-goal, which occurred in bizarre fashion after Japhet Tanganga's clearance bounced back off the Welshman's face into the net.

[79] The following weekend, Chelsea beat National League side Chesterfield 5–1 in the FA Cup third round in a match that saw Lewis Hall make his senior debut.

Chelsea only managed one shot on target during the entire game, and the result saw Manchester City move 13 points clear at the top of the Premier League table.

[85] The win meant that Chelsea had beaten Tottenham three times in the space of a month—the last Premier League team to achieve this feat was Aston Villa against Blackburn Rovers in January 2010.

[87] Chelsea began February with a 2–1 win after extra time against Plymouth Argyle in the FA Cup fourth round in a match led by assistant coach Arno Michels due to Tuchel's positive COVID-19 test.

Chelsea faced Saudi side Al-Hilal in the semi-finals at the Mohammed bin Zayed Stadium in Abu Dhabi in a match they won 1–0 courtesy of a goal from Romelu Lukaku.

[90] César Azpilicueta picked up the ball and appeared to be set to take the decisive penalty, but after being mobbed by Palmeiras players, he passed it to Kai Havertz, who scored.

[92] Chelsea returned to Premier League action on 19 February beating Crystal Palace 1–0 at Selhurst Park after Hakim Ziyech scored an 89th-minute winner.

[93] Three days later, Chelsea hosted their Champions League Round of 16 tie against Lille, winning 2–0 after goals from Kai Havertz, who replaced Lukaku in the starting lineup, and Christian Pulisic.

Mason Mount and Christian Pulisic both had opportunities to score in the first half, while Édouard Mendy made a series of important saves including one at point-blank range against Sadio Mané.

[99] After the game, Trevoh Chalobah openly criticised referee Stuart Attwell for failing to penalise a challenge from Naby Keïta which required stitches.

[102] In the following days, numerous reports about interested buyers surfaced including Swiss billionaire Hansjörg Wyss, Los Angeles Dodgers and Lakers shareholder Todd Boehly, Pakistani businessman Javed Afridi, and other unnamed parties.

[111][112] On 12 March, Chelsea's company credit cards were frozen, significantly limiting day-to-day spending but still allowing for matchday transportation costs lower than 20,000 per game.

[113] Technical director Petr Čech stated, "We have many questions, we don't have many answers but we are determined to concentrate on things we can control" and noted that the club was running "day-to-day.

[117][118][116] Prior to their trip to Lille for the second leg of the Champions League Round of 16, Thomas Tuchel noted that there were doubts about whether the team would be able to travel, stating "My last information is we are getting a plane.

[136] Before the second leg, Chelsea travelled to St. Mary's Stadium to take on Southampton, where they won 6–0 courtesy of braces from Timo Werner and Mason Mount and goals from Kai Havertz and Marcos Alonso.

[140] They returned to Premier League action with a 4–2 defeat to Arsenal at home on 20 April, with several defensive errors proving costly as the Gunners won at Stamford Bridge for the second consecutive season.

[143][144] During this period, it was widely reported that Antonio Rüdiger had agreed to join Real Madrid when his contract expired in the summer and would be leaving the club at the end of the season.

[145][146] Chelsea began the month of May with a 1–0 defeat to relegation-threatened Everton at Goodison Park, who were managed by former head coach and club legend Frank Lampard.

[150] The sale of Chelsea officially proceeded on 6 May, as an ownership group led by Todd Boehly, Clearlake Capital, Mark Walter, and Hansjörg Wyss acquired the club.

However, in the seventh round of spot kicks, Alisson saved Mason Mount's penalty, and Kostas Tsimikas scored, winning the FA Cup Final for Liverpool.

[160][161][162] Following the disappointment in the Cup Final, Chelsea were boosted by the fact that Arsenal lost back-to-back matches against Tottenham and Newcastle, guaranteeing them a top four finish and a spot in the 2022–23 UEFA Champions League.