Leicestershire clubs entered the Northamptonshire & District Challenge Cup in 1885 and 1886. The following season (1887-88), Leicestershire had its own challenge cup competition.
Winners and Runners-Up (1883-1900)
Season | Winner | Runner-Up | |
Rushden Wanderers | Bedford Town | Leicester Town (R2) Market Harborough (R1) | |
Wellingborough | Rushden | Leicester Town (SF) Market Harborugh (R1) | |
1887-88 | Rushden | Wellingborough | |
1888-89 | Wellingborough Grammar School | Rushden | |
1889-90 | Wellingborough Grammar School | Rushden | |
1890-91 | Finedon | Rushden | |
1891-92 | Finedon | Wellingborough Grammar School | |
1892-93 | Rushden | Finedon | |
1893-94 | Finedon | Peterborough King's School | |
1894-95 | Rushden | Kettering Town | |
1895-96 | Kettering | Rushden Town | |
1896-97 | Wellingborough | Rushden | |
1897-98 | Kettering | Wellingborough | |
1898-99 | Wellingborough | Northampton Town | |
1899-00 | Rothwell | Raunds United |