| | 27/04/2019 | Oakham 2 | 127-10 | 4 | | Asian Sports 2 | 209-7 | 25 | Aftab Ghanchi 127
Mignesh Tandel 63n.o. | 3895000 |
| | 18/05/2019 | Countesthorpe 2 | 166-6 | 25 | D. Page 4-28, Vas 48, Craigo 55* | Oakham 2 | 163-10 | 9 | | 3894972 |
| | 20/07/2019 | Oakham 2 | 208-8 | 25 | Owen 42 and 3-21 | Countesthorpe 2 | 119-7 | 11 | (144) R Looms 3-38, S Page 3-47 | 3895003 |
| | 27/07/2019 | Cosby | 0-0 | 5 | Match Abandoned Abandoned due to rain | Oakham 2 | 0-0 | 5 | Match Abandoned Abandoned due to rain | 3894983 |
| | 03/08/2019 | Oakham 2 | 195-9 | 8 | D Pegg 12-4-32-5, M Owen 53 | Thorpe Arnold 2 | 200-4 | 25 | L Perry 45 | 3895005 |
| | 10/08/2019 | Oakham 2 | 67-0 | 25 | W Begy 30* W Stuart-Jones 26* | Leicester Caribbean 2 | 66-10 | 0 | D Jones 12-3-18-5
A Owen 4.2-2-5-4 (incl hat-trick) | 3895007 |
| | 24/08/2019 | Oakham 2 | 189-10 | 25 | M Williams 64 O Hubbard 49 | Wigston Town | 152-10 | 11 | | 3894997 |
| | 14/09/2019 | Oakham 2 | 206-7 | 25 | B Southern 102* W Stuart-Jones 52 D Ramshaw 5-25 | Market Overton | 130-10 | 5 | | 3894999 |