| 10 May 2014 | | Cowdrey Second XI v Betteshanger Colliery Welfare Second XI | Swanmead Sports Ground, Tonbridge | Results |
| 10 May 2014 | | Deal Victoria and Barns Close Second XI v Bromley Town Second XI | Gun Meadow, Walmer | Results |
| 10 May 2014 | | Frindsbury Second XI v Offham Second XI | Frogs Island, Frindsbury | Results |
| 10 May 2014 | | High Halstow Second XI v Bexleyheath Second XI | Rayners Meadow, High Halstow | Results |
| 10 May 2014 | | Shooters Hill Second XI v Ashford Town Second XI | Old Shootershillian Sports and Social Club Ground, Kidbrooke | Results |
| 17 May 2014 | | Ashford Town Second XI v Deal Victoria and Barns Close Second XI | Stacians Park, Ashford | Results |
| 17 May 2014 | | Betteshanger Colliery Welfare Second XI v Shooters Hill Second XI | Welfare Ground, Deal | Results |
| 17 May 2014 | | Bexleyheath Second XI v Cowdrey Second XI | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 17 May 2014 | | Bromley Town Second XI v Frindsbury Second XI | Hayes Lane Cricket Ground, Bromley | Results |
| 17 May 2014 | | Offham Second XI v High Halstow Second XI | Church Road, Offham | Results |
| 24 May 2014 | | Bromley Town Second XI v Offham Second XI | Hayes Lane Cricket Ground, Bromley | Results |
| 24 May 2014 | | Cowdrey Second XI v Ashford Town Second XI | Swanmead Sports Ground, Tonbridge | Results |
| 24 May 2014 | | Deal Victoria and Barns Close Second XI v Shooters Hill Second XI | Gun Meadow, Walmer | Results |
| 24 May 2014 | | Frindsbury Second XI v Bexleyheath Second XI | Frogs Island, Frindsbury | Results |
| 24 May 2014 | | High Halstow Second XI v Betteshanger Colliery Welfare Second XI | Rayners Meadow, High Halstow | Results |
| 31 May 2014 | | Ashford Town Second XI v High Halstow Second XI | Stacians Park, Ashford | Results |
| 31 May 2014 | | Betteshanger Colliery Welfare Second XI v Frindsbury Second XI | Welfare Ground, Deal | Results |
| 31 May 2014 | | Bexleyheath Second XI v Bromley Town Second XI | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 31 May 2014 | | Offham Second XI v Deal Victoria and Barns Close Second XI | Church Road, Offham | Results |
| 31 May 2014 | | Shooters Hill Second XI v Cowdrey Second XI | Old Shootershillian Sports and Social Club Ground, Kidbrooke | Results |
| 07 Jun 2014 | | Bromley Town Second XI v Ashford Town Second XI | Hayes Lane Cricket Ground, Bromley | Results |
| 07 Jun 2014 | | Deal Victoria and Barns Close Second XI v Bexleyheath Second XI | Gun Meadow, Walmer | Results |
| 07 Jun 2014 | | Frindsbury Second XI v Shooters Hill Second XI | Frogs Island, Frindsbury | Results |
| 07 Jun 2014 | | High Halstow Second XI v Cowdrey Second XI | Rayners Meadow, High Halstow | Results |
| 07 Jun 2014 | | Offham Second XI v Betteshanger Colliery Welfare Second XI | Church Road, Offham | Results |
| 14 Jun 2014 | | Ashford Town Second XI v Frindsbury Second XI | Stacians Park, Ashford | Results |
| 14 Jun 2014 | | Betteshanger Colliery Welfare Second XI v Bromley Town Second XI | Welfare Ground, Deal | Results |
| 14 Jun 2014 | | Bexleyheath Second XI v Offham Second XI | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 14 Jun 2014 | | Cowdrey Second XI v Deal Victoria and Barns Close Second XI | Swanmead Sports Ground, Tonbridge | Results |
| 14 Jun 2014 | | Shooters Hill Second XI v High Halstow Second XI | Old Shootershillian Sports and Social Club Ground, Kidbrooke | Results |
| 21 Jun 2014 | | Ashford Town Second XI v Betteshanger Colliery Welfare Second XI | Stacians Park, Ashford | Results |
| 21 Jun 2014 | | Cowdrey Second XI v Offham Second XI | Swanmead Sports Ground, Tonbridge | Results |
| 21 Jun 2014 | | Frindsbury Second XI v Deal Victoria and Barns Close Second XI | Frogs Island, Frindsbury | Results |
| 21 Jun 2014 | | High Halstow Second XI v Bromley Town Second XI | Rayners Meadow, High Halstow | Results |
| 21 Jun 2014 | | Shooters Hill Second XI v Bexleyheath Second XI | Old Shootershillian Sports and Social Club Ground, Kidbrooke | Results |
| 28 Jun 2014 | | Bexleyheath Second XI v Betteshanger Colliery Welfare Second XI | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 28 Jun 2014 | | Bromley Town Second XI v Shooters Hill Second XI | Hayes Lane Cricket Ground, Bromley | Results |
| 28 Jun 2014 | | Deal Victoria and Barns Close Second XI v High Halstow Second XI | Gun Meadow, Walmer | Results |
| 28 Jun 2014 | | Frindsbury Second XI v Cowdrey Second XI | Frogs Island, Frindsbury | Results |
| 28 Jun 2014 | | Offham Second XI v Ashford Town Second XI | Church Road, Offham | Results |
| 05 Jul 2014 | | Ashford Town Second XI v Bexleyheath Second XI | Stacians Park, Ashford | Results |
| 05 Jul 2014 | | Betteshanger Colliery Welfare Second XI v Deal Victoria and Barns Close Second XI | Welfare Ground, Deal | Results |
| 05 Jul 2014 | | Cowdrey Second XI v Bromley Town Second XI | Swanmead Sports Ground, Tonbridge | Results |
| 05 Jul 2014 | | High Halstow Second XI v Frindsbury Second XI | Rayners Meadow, High Halstow | Results |
| 05 Jul 2014 | | Shooters Hill Second XI v Offham Second XI | Old Shootershillian Sports and Social Club Ground, Kidbrooke | Results |
| 12 Jul 2014 | | Ashford Town Second XI v Shooters Hill Second XI | Stacians Park, Ashford | Results |
| 12 Jul 2014 | | Betteshanger Colliery Welfare Second XI v Cowdrey Second XI | Welfare Ground, Deal | Results |
| 12 Jul 2014 | | Bexleyheath Second XI v High Halstow Second XI | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 12 Jul 2014 | | Bromley Town Second XI v Deal Victoria and Barns Close Second XI | Hayes Lane Cricket Ground, Bromley | Results |
| 12 Jul 2014 | | Offham Second XI v Frindsbury Second XI | Church Road, Offham | Results |
| 19 Jul 2014 | | Cowdrey Second XI v Bexleyheath Second XI | Swanmead Sports Ground, Tonbridge | Results |
| 19 Jul 2014 | | Deal Victoria and Barns Close Second XI v Ashford Town Second XI | Gun Meadow, Walmer | Results |
| 19 Jul 2014 | | Frindsbury Second XI v Bromley Town Second XI | Frogs Island, Frindsbury | Results |
| 19 Jul 2014 | | High Halstow Second XI v Offham Second XI | Rayners Meadow, High Halstow | Results |
| 19 Jul 2014 | | Shooters Hill Second XI v Betteshanger Colliery Welfare Second XI | Old Shootershillian Sports and Social Club Ground, Kidbrooke | Results |
| 26 Jul 2014 | | Ashford Town Second XI v Cowdrey Second XI | Stacians Park, Ashford | Results |
| 26 Jul 2014 | | Betteshanger Colliery Welfare Second XI v High Halstow Second XI | Welfare Ground, Deal | Results |
| 26 Jul 2014 | | Bexleyheath Second XI v Frindsbury Second XI | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 26 Jul 2014 | | Offham Second XI v Bromley Town Second XI | Church Road, Offham | Results |
| 26 Jul 2014 | | Shooters Hill Second XI v Deal Victoria and Barns Close Second XI | Old Shootershillian Sports and Social Club Ground, Kidbrooke | Results |
| 02 Aug 2014 | | Bromley Town Second XI v Bexleyheath Second XI | Hayes Lane Cricket Ground, Bromley | Results |
| 02 Aug 2014 | | Cowdrey Second XI v Shooters Hill Second XI | Swanmead Sports Ground, Tonbridge | Results |
| 02 Aug 2014 | | Deal Victoria and Barns Close Second XI v Offham Second XI | Gun Meadow, Walmer | Results |
| 02 Aug 2014 | | Frindsbury Second XI v Betteshanger Colliery Welfare Second XI | Frogs Island, Frindsbury | Results |
| 02 Aug 2014 | | High Halstow Second XI v Ashford Town Second XI | Rayners Meadow, High Halstow | Results |
| 09 Aug 2014 | | Ashford Town Second XI v Bromley Town Second XI | Stacians Park, Ashford | Results |
| 09 Aug 2014 | | Betteshanger Colliery Welfare Second XI v Offham Second XI | Welfare Ground, Deal | Results |
| 09 Aug 2014 | | Bexleyheath Second XI v Deal Victoria and Barns Close Second XI | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 09 Aug 2014 | | Cowdrey Second XI v High Halstow Second XI | Swanmead Sports Ground, Tonbridge | Results |
| 09 Aug 2014 | | Shooters Hill Second XI v Frindsbury Second XI | Old Shootershillian Sports and Social Club Ground, Kidbrooke | Results |
| 16 Aug 2014 | | Bromley Town Second XI v Betteshanger Colliery Welfare Second XI | Hayes Lane Cricket Ground, Bromley | Results |
| 16 Aug 2014 | | Deal Victoria and Barns Close Second XI v Cowdrey Second XI | Gun Meadow, Walmer | Results |
| 16 Aug 2014 | | Frindsbury Second XI v Ashford Town Second XI | Frogs Island, Frindsbury | Results |
| 16 Aug 2014 | | High Halstow Second XI v Shooters Hill Second XI | Rayners Meadow, High Halstow | Results |
| 16 Aug 2014 | | Offham Second XI v Bexleyheath Second XI | Church Road, Offham | Results |
| 23 Aug 2014 | | Betteshanger Colliery Welfare Second XI v Ashford Town Second XI | Welfare Ground, Deal | Results |
| 23 Aug 2014 | | Bexleyheath Second XI v Shooters Hill Second XI | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 23 Aug 2014 | | Bromley Town Second XI v High Halstow Second XI | Hayes Lane Cricket Ground, Bromley | Results |
| 23 Aug 2014 | | Deal Victoria and Barns Close Second XI v Frindsbury Second XI | Gun Meadow, Walmer | Results |
| 23 Aug 2014 | | Offham Second XI v Cowdrey Second XI | Church Road, Offham | Results |
| 30 Aug 2014 | | Ashford Town Second XI v Offham Second XI | Stacians Park, Ashford | Results |
| 30 Aug 2014 | | Betteshanger Colliery Welfare Second XI v Bexleyheath Second XI | Welfare Ground, Deal | Results |
| 30 Aug 2014 | | Cowdrey Second XI v Frindsbury Second XI | Swanmead Sports Ground, Tonbridge | Results |
| 30 Aug 2014 | | High Halstow Second XI v Deal Victoria and Barns Close Second XI | Rayners Meadow, High Halstow | Results |
| 30 Aug 2014 | | Shooters Hill Second XI v Bromley Town Second XI | Old Shootershillian Sports and Social Club Ground, Kidbrooke | Results |
| 06 Sep 2014 | | Bexleyheath Second XI v Ashford Town Second XI | Bexleyheath Sports Club Ground, Bexleyheath | Results |
| 06 Sep 2014 | | Bromley Town Second XI v Cowdrey Second XI | Hayes Lane Cricket Ground, Bromley | Results |
| 06 Sep 2014 | | Deal Victoria and Barns Close Second XI v Betteshanger Colliery Welfare Second XI | Gun Meadow, Walmer | Results |
| 06 Sep 2014 | | Frindsbury Second XI v High Halstow Second XI | Frogs Island, Frindsbury | Results |
| 06 Sep 2014 | | Offham Second XI v Shooters Hill Second XI | Church Road, Offham | Results |
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