| | 11/05/2019 | Newtown Linford | 188-9 | 12 | (204) Scaysbrook 48, Oliver 42; Chambers 3-46 | Oakham | 219-9 | 25 | Tattersall 91 & 3-28, Taylor 3-23 | 3892273 |
| | 25/05/2019 | Enderby | 168-10 | 3 | Turner 41* | Oakham | 287-7 | 25 | Cowley 67
Morris 69*
Lakhami 43
Jones 9-1-38-4 | 3892295 |
| | 01/06/2019 | Oakham | 287-5 | 25 | Shaun Morris 63, Wes Durston 62, Ed Tattersall 58, Cam Flowers 46 | Hinckley Town | 283-8 | 10 | Janak Valand 136* | 3892314 |
| | 29/06/2019 | Earl Shilton | 171-10 | 2 | Z Potter 44
W Durstan 6.2-3-5-3 | Oakham | 311-5 | 25 | W Durston 181 | 3892351 |
| | 06/07/2019 | Electricity Sports | 119-10 | 3 | Game reduced to 35 overs a side | Oakham | 277-7 | 25 | R.Taylor 125 chanceless | 3892384 |
| | 13/07/2019 | Oakham | 220-10 | 9 | | Newtown Linford | 221-4 | 25 | Lascu 4-38, Scaysbrook 3-34; Gale 74, Lowe 65no | 3892304 |
| | 20/07/2019 | Hinckley Amateur | 219-6 | 14 | A York 60 W Durston 9-1-30-2 | Oakham | 222-9 | 25 | C Flowers 80 M Butterworth 9-0-46-4 | 3892284 |
| | 14/09/2019 | Uppingham Town | 229-5 | 9 | J Dumford 65 B Farnsworth 69 | Oakham | 233-4 | 25 | W Durston 90 R Taylor 89 | 3892362 |