| Club: | Chelsea |
| Season: | 1965–66 |
| Manager: | Tommy Docherty |
| Chairman: | Joe Mears |
| League: | First Division |
| League Result: | 5th |
| Cup1: | FA Cup |
| Cup1 Result: | Semi-finals |
| Cup2: | Football League Cup |
| Cup2 Result: | DNE[1] |
| Cup3: | Inter-Cities Fairs Cup |
| Cup3 Result: | Semi-finals |
| Pattern B1: | _chelsea1965h |
| Leftarm1: | 0000FF |
| Body1: | FFFFFF |
| Rightarm1: | 0000FF |
| Shorts1: | 0000FF |
| Socks1: | ffffff |
| Pattern B2: | _qpr1415t |
| Leftarm2: | FFFFFF |
| Body2: | FFFFFF |
| Rightarm2: | FFFFFF |
| Shorts2: | FFFFFF |
| Socks2: | ffffff |
| Pattern La3: | _chelsea1965a2 |
| Pattern B3: | _chelsea1965a2 |
| Pattern Ra3: | _chelsea1965a2 |
| Leftarm3: | FFFFFF |
| Body3: | FFFFFF |
| Rightarm3: | FFFFFF |
| Shorts3: | 0000FF |
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| League Topscorer: | George Graham (17) |
| Season Topscorer: | George Graham, Bobby Tambling (23) |
| Highest Attendance: | 60,269 vs Manchester United (12 March 1966) |
| Lowest Attendance: | 10,024 vs Blackburn Rovers (4 May 1966) |
| Prevseason: | 1964–65 |
| Nextseason: | 1966–67 |
The 1965–66 season was Chelsea Football Club's 52nd of competitive football, and their 39th in the English top flight.
| Date | Opponent | Venue | Result | Attendance | Scorers | |
|---|---|---|---|---|---|---|
| 21 August 1965 | Burnley | H | 1–1 | 34,067 | Venables | |
| 25 August 1965 | Stoke City | A | 2–2 | 28,549 | Venables (pen), Tambling | |
| 28 August 1965 | Fulham | A | 3–0 | 34,027 | Murray, Graham, Bridges | |
| 1 September 1965 | Stoke City | H | 1–2 | 25,071 | Hollins | |
| 4 September 1965 | Arsenal | A | 3–1 | 45,456 | Graham, Bridges, Fascione | |
| 11 September 1965 | Everton | H | 3–1 | 29,816 | Graham, Bridges, Venables | |
| 15 September 1965 | Sheffield Wednesday | H | 1–1 | 26,183 | Venables | |
| 18 September 1965 | Manchester United | A | 1–4 | 37,917 | Venables | |
| 25 September 1965 | Newcastle United | H | 1–1 | 30,856 | Graham | |
| 2 October 1965 | West Bromwich Albion | A | 2–1 | 23,049 | Graham, Bridges | |
| 9 October 1965 | Blackpool | H | 0–1 | 28,022 | ||
| 16 October 1965 | Blackburn Rovers | A | 1–0 | 16,167 | Graham | |
| 23 October 1965 | Leicester City | H | 0–2 | 30,400 | ||
| 30 October 1965 | Sheffield United | A | 2–1 | 20,795 | Graham, Osgood | |
| 6 November 1965 | Leeds United | H | 1–0 | 39,373 | Hollins | |
| 13 November 1965 | West Ham United | A | 1–2 | 31,551 | Tambling | |
| 27 November 1965 | Aston Villa | A | 4–2 | 16,355 | Graham, Osgood, Tambling (2) | |
| 4 December 1965 | Liverpool | H | 0–1 | 36,839 | ||
| 11 December 1965 | Tottenham Hotspur | A | 2–4 | 42,299 | Bridges, Graham | |
| 27 December 1965 | Northampton Town | A | 3–2 | 23,325 | Graham, Tambling (2) | |
| 28 December 1965 | Northampton Town | H | 1–0 | 17,635 | Bridges | |
| 1 January 1966 | Blackpool | A | 2–1 | 14,065 | Graham, Tambling | |
| 8 January 1966 | Tottenham Hotspur | H | 2–1 | 48,529 | Graham, Osgood | |
| 29 January 1966 | Burnley | A | 2–1 | 23,825 | Osgood (2) | |
| 5 February 1966 | Fulham | H | 2–1 | 34,247 | Osgood, Tambling | |
| 19 February 1966 | Arsenal | H | 0–0 | 48,641 | ||
| 22 February 1966 | Sunderland | H | 3–2 | 20,828 | Bridges, Graham, Osgood | |
| 26 February 1966 | Everton | A | 1–2 | 51,298 | Bridges | |
| 12 March 1966 | Manchester United | H | 2–0 | 60,269 | Graham, Tambling | |
| 19 March 1966 | Newcastle United | A | 1–0 | 35,100 | Venables | |
| 21 March 1966 | Leicester City | A | 1–1 | 25,363 | Bridges | |
| 4 April 1966 | Leeds United | A | 0–2 | 37,786 | ||
| 9 April 1966 | West Ham United | H | 6–2 | 35,958 | Graham (2), Venables (pen), Tambling (2), R. Harris | |
| 11 April 1966 | Nottingham Forest | H | 1–0 | 39,380 | Tambling | |
| 12 April 1966 | Nottingham Forest | A | 2–1 | 29,569 | Tambling (2) | |
| 16 April 1966 | Sunderland | A | 0–2 | 32,880 | ||
| 25 April 1966 | West Bromwich Albion | H | 2–3 | 22,804 | Venables (pen), Tambling | |
| 30 April 1966 | Liverpool | A | 1–2 | 53,754 | Murray | |
| 2 May 1966 | Sheffield Wednesday | A | 1–1 | 26,777 | R. Harris | |
| 4 May 1966 | Blackburn Rovers | H | 1–0 | 10,024 | Kirkup | |
| 7 May 1966 | Sheffield United | H | 2–0 | 23,072 | Graham, Tambling | |
| 16 May 1966 | Aston Villa | H | 0–2 | 16,232 |
| Date | Round | Opponent | Venue | Result | Attendance | Scorers | |
|---|---|---|---|---|---|---|---|
| 22 January 1965 | 3 | Liverpool | A | 2–1 | 54,097 | Osgood, Tambling | |
| 12 February 1965 | 4 | Leeds United | H | 1–0 | 57,847 | Tambling | |
| 5 March 1965 | 5 | Shrewsbury Town | H | 3–2 | 51,144 | Bridges (2), Graham | |
| 26 March 1965 | QF | Hull City | H | 2–2 | 46,924 | Graham, Tambling | |
| 31 March 1965 | QF (R) | Hull City | A | 3–1 | 45,328 | Graham, Tambling (2) | |
| 23 April 1965 | SF | Sheffield Wednesday | N | 0–2 | 61,321 |
| Date | Round | Opponent | Venue | Result | Attendance | Scorers | |
|---|---|---|---|---|---|---|---|
| 22 September 1965 | 1 | Roma | H | 4–1 | 32,753 | Graham, Venables (3) | |
| 6 October 1965 | 1 | Roma | A | 0–0 | 40,000 | ||
| 7 November 1965 | 2 | Wiener Sport-Club | A | 0–1 | 4,000 | ||
| 1 December 1965 | 2 | Wiener Sport-Club | H | 2–0 | 28,254 | Murray, Osgood | |
| 9 February 1966 | 3 | AC Milan | A | 1–2 | 11,411 | Graham | |
| 16 February 1966 | 3 | AC Milan | H | 2–1 | 59,541 | Graham, Osgood | |
| 2 March 1966 | 3 (R) | AC Milan | A | 1–1 | 30,620 | Bridges | |
| 2 March 1966 | AC Milan | Chelsea won on coin toss | |||||
| 15 March 1966 | QF | 1860 München | A | 2–2 | 11,000 | Tambling (2) | |
| 29 March 1966 | QF | 1860 München | H | 1–0 | 42,224 | Osgood | |
| 27 April 1966 | SF | Barcelona | A | 0–2 | 70,000 | ||
| 11 May 1966 | SF | Barcelona | H | 2–0 | 40,073 | Reina (o.g.), Gallego (o.g.) | |
| 25 May 1966 | SF (R) | Barcelona | A | 0–5 | 40,000 |