| | 11/05/2019 | Uppingham Town | 162-5 | 25 | (160) B Farnsworth 59 | Leicester Ivanhoe 2 | 180-10 | 9 | A Carrie 50
O Winder 52 NO | 3892365 |
| | 22/06/2019 | Hinckley Amateur | 156-10 | 25 | York 47. Ashwin 6-1-12-3 | Uppingham Town | 113-10 | 10 | Hodson 43. Jackson 7.3-1-37-3 / Butterworth 4-2-19-4 | 3892289 |
| | 20/07/2019 | Uppingham Town | 117-10 | 25 | J Dumford 42
A Ashwin 7.3-2-12-5 | Earl Shilton | 35-10 | 6 | | 3892366 |
| | 03/08/2019 | Kibworth 2 | 226-8 | 25 | Raja Hayat 79
Harry Pounds 55 | Uppingham Town | 139-10 | 5 | | 3892378 |
| | 17/08/2019 | Newtown Linford | 161-7 | 25 | Lascu 5-38; Woods 76, Gale 45 | Uppingham Town | 160-10 | 10 | | 3892278 |
| | 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 |