| Club: | Chelsea |
| Season: | 1958–59 |
| Manager: | Ted Drake |
| Chairman: | Joe Mears |
| Stadium: | Stamford Bridge |
| League: | First Division |
| League Result: | 14th |
| Cup1: | FA Cup |
| Cup1 Result: | Fourth round |
| Cup2: | Inter-Cities Fairs Cup |
| Cup2 Result: | Quarter-finals |
| League Topscorer: | Jimmy Greaves (32) |
| Season Topscorer: | Jimmy Greaves (37) |
| Largest Win: | 6–2 v Wolves |
| Largest Loss: | 0–6 v Bolton Wanderers |
| Highest Attendance: | |
| Lowest Attendance: | |
| Pattern B1: | _whitecollarplain |
| Pattern So1: | _whitetop |
| Leftarm1: | 0000ff |
| Body1: | 0000ff |
| Rightarm1: | 0000ff |
| Socks1: | 000000 |
| Pattern B2: | _whitecollarplain |
| Pattern So2: | _whitetop |
| Leftarm2: | ff0000 |
| Body2: | ff0000 |
| Rightarm2: | ff0000 |
| Socks2: | 000000 |
| Prevseason: | 1957–58 |
| Nextseason: | 1959–60 |
The 1958–59 season was Chelsea Football Club's 45th competitive season. The club played in the European competition for the first time, and reached the quarter-finals of the Inter-Cities Fairs Cup, where they lost on aggregate to a Belgrade XI. With 32 league goals, Jimmy Greaves was the First Division's top goalscorer, becoming the first Chelsea played to achieve this.