The 1960- 61 campaign proved to be the last one with Ted Drake in charge at Chelsea. The Blues had a moderate league season, finishing off in a reasonable 12th place. The blues reached the fourth round of the first ever league cup and suffered a narrow defeat against Portsmouth FC. Jimmy Greaves was in the most incredible prolific form through out the campaign, scoring a phenomenal 41 goals during the season, the most league goals ever scored by a Chelsea player in a single season. Tommy Docherty took charge at the club during the 1961 – 62 league season, however, the team suffered a very poor league season, finishing the campaign off in a poor 22nd place. They were part of a thrilling FA cup tie which they lost 4-3 against Liverpool in the third round. The 1962 -63 campaign saw the Blues bounce right back up as they were in fine form in the second division as they finished off in second position and Bobby Tambling was in prolific form for the club, a player who would go on to score 164 league goals during his 12 year stay. The 1962 – 63 campaign was also notable for the debut of Ron Harris, a Chelsea superstar who would go on to make 655 league appearances in an 18 year career at the club between 1962 and 1980. Tommy Docherty took the Blues to incredible heights during the 1963 -64 season as they were emphatic in the top flight, finishing the season off in fifth place, adjusting immediately back into the top flight in the finest fashion.
The 1964- 65 season was one of the finest in the history of the football club as they became a dominant force in British football. They were outstanding in the league, finishing off the campaign in third position and they reached the semi finals of the FA Cup, suffering a 2-0 defeat against Liverpool at Villa Park. They achieved an incredible triumph in the League cup, winning the competition for the first time, defeating Leicester City in the final played at Wembley.