| | | 4/19/2014 | Kegworth Town 2 | 152-6 | 6 | Luke Woolley 31, Glyn Isaac 31no, Ziab Khan 31no | Uppingham Town | 156-7 | 25 | Patrick Latham 57, A Ashwin 51 not out, Colan Bartram 3 for 46 | 11879488 |
| | | 4/26/2014 | Uppingham Town | 201-9 | 7 | | Illston Abey | 202-4 | 25 | Irfan 72 N.O
Emran 86 N.O
| 11879560 |
| | | 5/3/2014 | Newtown Linford 2 | 211-10 | 30 | Kingham 103, Shepherd 33, Ashwin 3-31, Wade 3-21 | Uppingham Town | 77-10 | 5 | Saxby 7-21 | 11879510 |
| | | 5/10/2014 | Uppingham Town | 156-2 | 25 | Jamie Dumford 88 NO
Patrick Latham 12-5-20-3 Daniel Dumford 8-3-26-3
| Mountsorrel Castle | 155-8 | 4 | Shabaz 58 NO | 11879562 |
| | | 6/7/2014 | Quorn | 84-10 | 5 | Ross Errington 4-47
Dominic Watts 40 | Uppingham Town | 124-10 | 30 | Pat Latham 4-19 | 11879588 |
| | | 6/14/2014 | Uppingham Town | 239-7 | 21 | Game Reduced to 43 overs a side
, M Cox 104 no, J Dumford 49
| Oakham | 126-9 | 6 | Game Reduced to 43 overs a side, C Flowers 37, D Jones 3-66 | 11879566 |
| | | 6/28/2014 | Uppingham Town | 98-10 | 5 | D Dumford 3-47 P Latham 4-31 | Egerton Park | 108-10 | 30 | N Watchorn 5-21 | 11879558 |
| | | 7/5/2014 | Uppingham Town | 196-7 | 11 | J Dumford 46
P Latham 12-3-19-3 | Newtown Linford 2 | 221-6 | 17 | D Bulpitt 81
D Kingham 70 | 11879561 |
| | | 7/12/2014 | Mountsorrel Castle | 107-10 | 4 | J. Navsari 4-35 | Uppingham Town | 244-7 | 30 | S.Hodson 88 D.Domford 62 N.O S.Green 4-8 | 11879521 |
| | | 7/19/2014 | Uppingham Town | 184-6 | 25 | S Green 4-49
C Bartram 4-42
M Bennett 101 no | Syston Town 2 | 181-9 | 7 | B Coddington 70
S Cooper 4-27 | 11879563 |
| | | 7/26/2014 | Electricity Sports | 207-9 | 8 | R.Wright 50
A.Deacon 51
M.Sheppard 47 no | Uppingham Town | 208-6 | 25 | D.Butchart 57 | 11879543 |
| | | 8/2/2014 | Uppingham Town | 169-10 | 18 | Game Reduced to 37 Overs
A Ashwin 10-3-27-3 | Houghton & Thurnby 2 | 100-7 | 7 | Game Reduced to 37 Overs
J Wigley 7-1-25-4 | 11879565 |
| | | 8/9/2014 | Uppingham Town | 123-6 | 25 | M Cox 46
A Ashwin 4-36
D Dumford 3-30 | Quorn | 122-10 | 4 | S Maddocks 2-28 | 11879567 |
| | | 8/23/2014 | Uppingham Town | 209-7 | 20 | S Hodson 63 no
D Dumford 51
P Latham 12-6-14-3 | Cosby | 122-6 | 5 | L Freer 31 | 11879557 |