| | 19/04/2014 | Uppingham Town 2 | 157-7 | 4 | Sam Cowling 43. Alan Brown 25. Charles Richardson 24 | Houghton & Thurnby 3 | 159-3 | 25 | Harry Funnell 62 no. I Meman 41no. | 11880026 |
| | 26/04/2014 | Great Glen | 160-10 | 30 | J Goddard 32 | Uppingham Town 2 | 63-10 | 5 | D Young 11.2 overs, 9 maidens, 3 wickets, 2 runs. | 11880088 |
| | 03/05/2014 | Uppingham Town 2 | 135-5 | 5 | Kashmir Munir 33 & 12-4-2-23
Joe Bennett 11-1-2-56 | Fleckney Village | 243-5 | 19 | T Brown 67
D Brown 36 no
J Loomes 31no | 11880028 |
| | 10/05/2014 | Dunton Bassett 2 | 55-1 | 25 | Shyam 5 for 19 Popat 3 for 18 | Uppingham Town 2 | 54-10 | 0 | | 11879988 |
| | 17/05/2014 | Uppingham Town 2 | 170-3 | 25 | Tom Hubbard 75no
Tom Roberts 57no A Salt 17 | Bitteswell 2 | 165-6 | 4 | R Pearson 34 R Ogden 36no G Fox 20 | 11880020 |
| | 31/05/2014 | Uppingham Town 2 | 119-1 | 25 | Jack Salt 60 no
J Bramachari 33
Joe Bennett 11-3-18-4
Pete Smith 12-1-39-3
Sam Rees 6-0-33-3 | Melton Mowbray 2 | 118-10 | 1 | | 11880029 |
| | 07/06/2014 | Uppingham Town 2 | 163-8 | 30 | Tom Scott 60 Sam Cowling 36
Will Armstrong 12-3-45-6 Roger Dumford 8-5-5-2 Sam Rees 6-2-1-9 | Electricity Sports 3 | 107-10 | 5 | D Willetts 9-0-37-2 Raikundalia 12-2-37-2 | 11880022 |
| | 14/06/2014 | Whetstone | 112-10 | 3 | S Mahapatra 62 | Uppingham Town 2 | 116-4 | 25 | C Bartram 12-3-20-4
D Butchalt 45 no
| 11880044 |
| | 21/06/2014 | Uppingham Town 2 | 141-5 | 25 | Tom Scott 52
Tom Roberts 6-2-21-1 W Armstrong 8-2-10-1 Joe Bennett 7-1-21-2 | Lutterworth 3 | 138-9 | 4 | G Baxter 49no
| 11880024 |
| | 05/07/2014 | Fleckney Village | 136-3 | 25 | C Atkinson 50 n.o. Adnan 11.2-1-36-5 | Uppingham Town 2 | 132-10 | 3 | | 11880099 |
| | 26/07/2014 | Uppingham Town 2 | 126-10 | 7 | A Salt 44 A Brown 34 T Roberts 10.5-4-22-4 S Rees 11-1-57-3 | Highfield Rangers | 218-10 | 30 | Tajwinder Singh 55, match winning performance by Raj Kahlon 10.2-3-17-8 | 11880021 |
| | 09/08/2014 | Electricity Sports 3 | 209-6 | 9 | F.Parkar 60
Catching practice for us this week. We dropped their last man when they were 9 down.
Nevertheless a great game played in good spirit | Uppingham Town 2 | 210-9 | 25 | A.Salt 55
S.Cowling 75 | 11880033 |
| | 16/08/2014 | Uppingham Town 2 | 127-2 | 25 | Will Armstrong 10.3-2-24-4. H Wade 6-0-43-2. S Rees 7-1-28-2
Joe Bennett 3-1-13-1. J Brahmachari 42. G Scott 64no. | Whetstone | 125-10 | 3 | J Lunn 27. Maharaja 30 | 11880023 |
| | 13/09/2014 | Uppingham Town 2 | 65-10 | 1 | | Great Glen | 66-2 | 25 | J Bennett 12-2-27-7
J Modhawdia 45no | 11880027 |