| City Cup | |
| Year: | 1958–59 |
| Num Teams: | 12 |
| Defending Champions: | Linfield |
| Winners: | Linfield (20th win) |
| Second: | Glenavon |
| Matches: | 69 |
| Goals: | 293 |
| Prev Season: | 1957–58 |
| Next Season: | 1959–60 |
The 1958–59 City Cup was the 54th edition of the City Cup, a cup competition in Northern Irish football.[1]
The tournament was won by Linfield for the 20th time and 2nd consecutive season. They defeated Glenavon 4–0 in a test match at Solitude after both teams finished level on points in the group standings.[2] [3]