| Season: | 1968–69 |
| League Result: | 5th |
| Cup1 Result: | Quarter-finals |
| Cup2 Result: | Third round |
| Cup3 Result: | Second round |
| Pattern B1: | _chelsea1965h |
| Leftarm1: | 0000FF |
| Body1: | FFFFFF |
| Rightarm1: | 0000FF |
| Shorts1: | 0000FF |
| Socks1: | ffffff |
| Pattern B2: | _chelsea1967a |
| Leftarm2: | FFFF00 |
| Body2: | FFFF00 |
| Rightarm2: | FFFF00 |
| Shorts2: | 0000FF |
| Socks2: | ffff00 |
| League Topscorer: | Bobby Tambling (18) |
| Season Topscorer: | Bobby Tambling (19) |
| Highest Attendance: | 60,436 vs Manchester United (15 March 1969) |
| Lowest Attendance: | 17,639 vs Coventry City (10 March 1969) |
| Prevseason: | 1967–68 |
| Nextseason: | 1969–70 |
The 1968–69 season was Chelsea Football Club's 55th of competitive football, and their 42nd in the English top flight.
| Date | Opponent | Venue | Result | Attendance | Scorers | |
|---|---|---|---|---|---|---|
| 14 August 1968 | Nottingham Forest | H | 1–1 | 36,515 | Tambling | |
| 17 August 1968 | West Bromwich Albion | H | 3–1 | 33,766 | Baldwin, Tambling (2) | |
| 21 August 1968 | Newcastle United | A | 2–3 | 39,048 | Tambling, Birchenall | |
| 24 August 1968 | Manchester United | A | 4–0 | 55,114 | Baldwin (2), Tambling, Birchenall | |
| 28 August 1968 | Sheffield Wednesday | H | 1–0 | 33,402 | Tambling | |
| 31 August 1968 | Tottenham Hotspur | H | 2–2 | 48,412 | Osgood (pen), Birchenall | |
| 7 September 1968 | Everton | H | 1–1 | 42,017 | Osgood (pen) | |
| 10 September 1968 | Coventry City | A | 1–0 | 36,217 | Osgood | |
| 14 September 1968 | Queens Park Rangers | A | 4–0 | 26,358 | Baldwin (2), Osgood, Birchenall | |
| 21 September 1968 | West Ham United | H | 1–1 | 58,062 | Tambling | |
| 28 September 1968 | Burnley | A | 1–2 | 14,762 | Tambling | |
| 5 October 1968 | Ipswich Town | H | 3–1 | 31,625 | Hollins, Birchenall, Baxter (o.g.) | |
| 9 October 1968 | Sheffield Wednesday | A | 1–1 | 30,445 | Baldwin | |
| 12 October 1968 | Wolverhampton Wanderers | A | 1–1 | 27,810 | Tambling | |
| 19 October 1968 | Leicester City | H | 3–0 | 33,462 | Baldwin (3) | |
| 26 October 1968 | Stoke City | A | 0–2 | 16,799 | ||
| 2 November 1968 | Manchester City | H | 2–0 | 40,700 | Osgood, Baldwin | |
| 9 November 1968 | Liverpool | A | 1–2 | 47,248 | Birchenall | |
| 16 November 1968 | Southampton | H | 2–3 | 31,325 | Baldwin, Birchenall | |
| 23 November 1968 | Arsenal | A | 1–0 | 45,588 | Houseman | |
| 30 November 1968 | Leeds United | H | 1–1 | 43,286 | Osgood | |
| 7 December 1968 | Sunderland | A | 2–3 | 21,976 | Birchenall, Baldwin | |
| 14 December 1968 | Wolverhampton Wanderers | H | 1–1 | 26,194 | Osgood (pen) | |
| 21 December 1968 | Leicester City | A | 4–1 | 23,597 | Osgood (2), Birchenall, Tambling | |
| 26 December 1968 | Ipswich Town | A | 3–1 | 24,083 | Webb (3) | |
| 11 January 1969 | Manchester City | A | 1–4 | 35,605 | Houseman | |
| 18 January 1969 | Liverpool | H | 1–2 | 52,295 | Tambling | |
| 1 February 1969 | Southampton | A | 0–5 | 28,147 | ||
| 15 February 1969 | Leeds United | A | 0–1 | 35,789 | ||
| 22 February 1969 | Sunderland | H | 5–1 | 29,381 | Birchenall, Tambling (4) | |
| 5 March 1969 | Stoke City | H | 1–0 | 19,856 | Webb | |
| 8 March 1969 | West Bromwich Albion | A | 3–0 | 25,137 | Boyle, Hutchinson, Houseman | |
| 10 March 1969 | Coventry City | H | 2–1 | 17,639 | Tambling, Hutchinson | |
| 15 March 1969 | Manchester United | H | 3–2 | 60,436 | Webb, Tambling, Hutchinson | |
| 22 March 1969 | Tottenham Hotspur | A | 0–1 | 47,349 | ||
| 29 March 1969 | Everton | A | 2–1 | 42,190 | Birchenall, Hutchinson | |
| 4 April 1969 | Newcastle United | H | 1–1 | 42,078 | Hutchinson | |
| 5 April 1969 | Burnley | H | 2–3 | 30,266 | Hollins, Tambling | |
| 8 April 1969 | Nottingham Forest | A | 2–1 | 30,413 | Birchenall, Hutchinson | |
| 12 April 1969 | West Ham United | A | 0–0 | 32,332 | ||
| 14 April 1969 | Arsenal | H | 2–1 | 37,890 | Webb, Baldwin | |
| 19 April 1969 | Queens Park Rangers | H | 2–1 | 41,263 | Baldwin (2) |
| Date | Round | Opponent | Venue | Result | Attendance | Scorers | |
|---|---|---|---|---|---|---|---|
| 4 January 1969 | 3 | Carlisle United | H | 2–0 | 37,322 | Osgood, Tambling | |
| 25 January 1969 | 4 | Preston North End | A | 0–0 | 31,875 | ||
| 3 February 1969 | 4 (R) | Preston North End | H | 2–1 | 36,522 | Webb, Cooke | |
| 12 February 1969 | 5 | Stoke City | H | 3–2 | 39,191 | Osgood (2), Birchenall | |
| 1 March 1969 | QF | West Bromwich Albion | H | 1–2 | 52,285 | Webb |
| Date | Round | Opponent | Venue | Result | Attendance | Scorers | |
|---|---|---|---|---|---|---|---|
| 3 September 1968 | 2 | Birmingham City | A | 1–0 | 31,560 | Foster (o.g.) | |
| 25 September 1968 | 3 | Derby County | H | 0–0 | 26,975 | ||
| 2 October 1968 | 3 (R) | Derby County | A | 1–3 | 34,463 | Birchenall |
| Date | Round | Opponent | Venue | Result | Attendance | Scorers | |
|---|---|---|---|---|---|---|---|
| 18 September 1968 | 1 | Greenock Morton | H | 5–0 | 28,736 | Hollins, Boyle, Cooke, Osgood, Birchenall | |
| 30 September 1968 | 1 | Greenock Morton | A | 4–3 | 8,000 | Baldwin, Tambling, Birchenall, Houseman | |
| 23 October 1968 | 2 | DWS | H | 0–0 | 28,428 | ||
| 30 October 1968 | 2 | DWS | A | 0–0 | 14,000 | ||
| 30 October 1968 | DWS | Chelsea lost on coin toss | |||||