| 06 Jul 1895 | | Lodge School v Leeward | Spartan Cricket Club Ground, Belleville | Results |
| 06 Jul 1895 | | Wanderers v Harrison College | The Bay, Bridgetown | Results |
| 06 Jul 1895 | | Windward v Spartan | Codrington College, St John | Results |
| 13 Jul 1895 | | Barbados Garrison v Lodge School | The Savannah, St Ann's Garrison | Results |
| 13 Jul 1895 | | Windward v Harrison College | Codrington College, St John | Results |
| 20 Jul 1895 | | Harrison College v Pickwick | Harrison College Ground, Bridgetown | Results |
| 20 Jul 1895 | | Wanderers v Barbados Garrison | The Bay, Bridgetown | Results |
| 20 Jul 1895 | | Windward v Leeward | Codrington College, St John | Results |
| 24 Jul 1895 | | Lodge School v Spartan | The Lodge School, Society | Results |
| 27 Jul 1895 | | Barbados Garrison v Windward | The Savannah, St Ann's Garrison | Results |
| 03 Aug 1895 | | Barbados Garrison v Pickwick | The Savannah, St Ann's Garrison | Results |
| 03 Aug 1895 | | Harrison College v Spartan | Harrison College Ground, Bridgetown | Results |
| 03 Aug 1895 | | Leeward v Lodge School | The Bay, Bridgetown | Results |
| 03 Aug 1895 | | Windward v Wanderers | Codrington College, St John | Results |
| 10 Aug 1895 | | Harrison College v Barbados Garrison | Harrison College Ground, Bridgetown | Results |
| 17 Aug 1895 | | Leeward v Spartan | Hannays Pasture, St Lucy | Results |
| 17 Aug 1895 | | Wanderers v Lodge School | The Bay, Bridgetown | Results |
| 17 Aug 1895 | | Windward v Pickwick | Codrington College, St John | Results |
| 23 Aug 1895 | | Pickwick v Harrison College | Pickwick Cricket Club, Bridgetown | Results |
| 14 Sep 1895 | | Spartan v Barbados Garrison | Spartan Cricket Club Ground, Belleville | Results |
| 28 Sep 1895 | | Barbados Garrison v Wanderers | The Savannah, St Ann's Garrison | Results |
| 28 Sep 1895 | | Pickwick v Leeward | Pickwick Cricket Club, Bridgetown | Results |
| 05 Oct 1895 | | Barbados Garrison v Leeward | The Savannah, St Ann's Garrison | Results |
| 05 Oct 1895 | | Pickwick v Lodge School | Pickwick Cricket Club, Bridgetown | Results |
| 12 Oct 1895 | | Harrison College v Leeward | Harrison College Ground, Bridgetown | Results |
| 12 Oct 1895 | | Lodge School v Barbados Garrison | The Lodge School, Society | Results |
| 12 Oct 1895 | | Spartan v Windward | Spartan Cricket Club Ground, Belleville | Results |
| 12 Oct 1895 | | Wanderers v Pickwick | The Bay, Bridgetown | Results |
| 19 Oct 1895 | | Harrison College v Windward | Harrison College Ground, Bridgetown | Results |
| 19 Oct 1895 | | Spartan v Lodge School | Spartan Cricket Club Ground, Belleville | Results |
| 26 Oct 1895 | | Harrison College v Wanderers | Harrison College Ground, Bridgetown | Results |
| 26 Oct 1895 | | Pickwick v Spartan | Pickwick Cricket Club, Bridgetown | Results |
| 26 Oct 1895 | | Windward v Lodge School | Codrington College, St John | Results |
| 02 Nov 1895 | | Harrison College v Lodge School | Harrison College Ground, Bridgetown | Results |
| 02 Nov 1895 | | Leeward v Wanderers | Hannays Pasture, St Lucy | Results |
| 02 Nov 1895 | | Windward v Barbados Garrison | Codrington College, St John | Results |
| 09 Nov 1895 | | Leeward v Harrison College | Hannays Pasture, St Lucy | Results |
| 23 Nov 1895 | | Leeward v Windward | Hannays Pasture, St Lucy | Results |
| 23 Nov 1895 | | Lodge School v Wanderers | The Lodge School, Society | Results |
| 27 Nov 1895 | | Pickwick v Barbados Garrison | Pickwick Cricket Club, Bridgetown | Results |
| 30 Nov 1895 | | Leeward v Pickwick | Hannays Pasture, St Lucy | Results |
| 30 Nov 1895 | | Lodge School v Harrison College | The Lodge School, Society | Results |
| 07 Dec 1895 | | Leeward v Barbados Garrison | Hannays Pasture, St Lucy | Results |
| 07 Dec 1895 | | Pickwick v Wanderers | Pickwick Cricket Club, Bridgetown | Results |
| 07 Dec 1895 | | Spartan v Harrison College | Spartan Cricket Club Ground, Belleville | Results |
| 14 Dec 1895 | | Barbados Garrison v Spartan | The Savannah, St Ann's Garrison | Results |
| 14 Dec 1895 | | Lodge School v Windward | The Lodge School, Society | Results |
| 04 Jan 1896 | | Pickwick v Windward | Pickwick Cricket Club, Bridgetown | Results |
| 04 Jan 1896 | | Spartan v Wanderers | Spartan Cricket Club Ground, Belleville | Results |
| 18 Jan 1896 | | Lodge School v Pickwick | The Lodge School, Society | Results |
| 18 Jan 1896 | | Wanderers v Leeward | The Bay, Bridgetown | Results |
| 01 Feb 1896 | | Barbados Garrison v Harrison College | The Savannah, St Ann's Garrison | Results |
| 01 Feb 1896 | | Spartan v Pickwick | Spartan Cricket Club Ground, Belleville | Results |
| 01 Feb 1896 | | Wanderers v Windward | The Bay, Bridgetown | Results |
| 15 Feb 1896 | | Wanderers v Spartan | The Bay, Bridgetown | Results |
| 29 Feb 1896 | | Spartan v Leeward | Spartan Cricket Club Ground, Belleville | Results |
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