| Millom v Oldham | September 9, 1899 | Lancashire Senior Competition | Won | 13 | 5 |
| Oldham v Tyldesley | September 16, 1899 | Lancashire Senior Competition | Won | 27 | 0 |
| Oldham v Runcorn | September 23, 1899 | Lancashire Senior Competition | Lost | 2 | 3 |
| Stockport v Oldham | September 25, 1899 | Lancashire Senior Competition | Won | 6 | 0 |
| Widnes v Oldham | October 7, 1899 | Lancashire Senior Competition | Won | 14 | 3 |
| Rochdale Hornets v Oldham | October 14, 1899 | Lancashire Senior Competition | Won | 17 | 2 |
| Oldham v Stockport | October 17, 1899 | Lancashire Senior Competition | Won | 16 | 5 |
| Oldham v Salford | October 28, 1899 | Lancashire Senior Competition | Won | 10 | 2 |
| Swinton v Oldham | November 11, 1899 | Lancashire Senior Competition | Won | 5 | 2 |
| Oldham v Warrington | November 18, 1899 | Lancashire Senior Competition | Won | 14 | 3 |
| Wigan v Oldham | November 25, 1899 | Lancashire Senior Competition | Won | 21 | 3 |
| St Helens v Oldham | December 9, 1899 | Lancashire Senior Competition | Lost | 14 | 17 |
| Broughton Rangers v Oldham | December 23, 1899 | Lancashire Senior Competition | Draw | 0 | 0 |
| Oldham v Rochdale Hornets | December 25, 1899 | Lancashire Senior Competition | Won | 9 | 0 |
| Oldham v Millom | December 30, 1899 | Lancashire Senior Competition | Won | 35 | 0 |
| Oldham v Leigh | January 6, 1900 | Lancashire Senior Competition | Won | 14 | 3 |
| Oldham v Widnes | January 13, 1900 | Lancashire Senior Competition | Won | 13 | 5 |
| Oldham v Wigan | January 20, 1900 | Lancashire Senior Competition | Won | 9 | 0 |
| Salford v Oldham | January 27, 1900 | Lancashire Senior Competition | Won | 6 | 0 |
| Oldham v Swinton | February 3, 1900 | Lancashire Senior Competition | Won | 17 | 2 |
| Oldham v Broughton Rangers | February 17, 1900 | Lancashire Senior Competition | Won | 21 | 3 |
| Warrington v Oldham | February 21, 1900 | Lancashire Senior Competition | Lost | 6 | 8 |
| Leigh v Oldham | February 24, 1900 | Lancashire Senior Competition | Won | 10 | 0 |
| Tyldesley v Oldham | February 27, 1900 | Lancashire Senior Competition | Won | 9 | 0 |
| Oldham v St Helens | March 3, 1900 | Lancashire Senior Competition | Won | 35 | 6 |
| Runcorn v Oldham | March 10, 1900 | Lancashire Senior Competition | Lost | 0 | 3 |
| Manningham v Oldham | March 17, 1900 | Rugby League Challenge Cup | Draw | 3 | 3 |
| Oldham v Manningham | March 20, 1900 | Rugby League Challenge Cup | Won | 18 | 3 |
| Halifax v Oldham | March 24, 1900 | Rugby League Challenge Cup | Won | 10 | 5 |
| Swinton v Oldham | March 31, 1900 | Rugby League Challenge Cup | Lost | 2 | 14 |
| Hull Kingston Rovers v Oldham | April 7, 1900 | Friendly | Won | 14 | 0 |
| Oldham v Brighouse Rangers | April 16, 1900 | Friendly | Lost | 0 | 3 |