1958-59 South East Counties League Cup
From TheChels.info - The Chelsea Football Club Wiki
Matches
| D | M | Year | Comp | Opposition | Venue | Result | Score | Additional information |
| 1 | Oct | 1958 | SECLC | Portsmouth | Home | Won | 5-1 | 1957-8 Final – 1st. Leg Played at Stamford Bri dge |
| 29 | Oct | 1958 | SECLC | Portsmouth | Away | Won | 8-1 | 1957-8 Final – 2nd. Leg |
| 18 | Oct | 1958 | SECLC | Crystal Palace | Home | Won | 2-1 | 1st. Round |
| 3 | Jan | 1959 | SECLC | Luton Town | Home | Won | 9-0 | 2nd. Round |
| 6 | Apr | 1959 | SECLC | Arsenal | Home | Won | 4-1 | Semi-Final Played at Stamford Bridge |
| 27 | Apr | 1959 | SECLC | Portsmouth | Home | Won | 4-1 | Final – 1st. Leg Played at Stamford Bridge |
| 29 | Apr | 1959 | SECLC | Portsmouth | Away | Won | 4-1 | Final – 2nd. Leg Chelsea won 8-2 on agg |