| 08 Jul 1905 | | Pickwick v Lodge School | Pickwick Cricket Club, Bridgetown | Results |
| 15 Jul 1905 | | Harrison College v Lodge School | Harrison College Ground, Bridgetown | Results |
| 22 Jul 1905 | | Barbados Garrison v Spartan | The Savannah, St Ann's Garrison | Results |
| 22 Jul 1905 | | Lodge School v Wanderers | The Lodge School, Society | Results |
| 22 Jul 1905 | | Pickwick v Harrison College | Pickwick Cricket Club, Bridgetown | Results |
| 29 Jul 1905 | | Lodge School v Barbados Garrison | The Lodge School, Society | Results |
| 29 Jul 1905 | | Wanderers v Harrison College | The Bay, Bridgetown | Results |
| 05 Aug 1905 | | Lodge School v Harrison College | The Lodge School, Society | Results |
| 05 Aug 1905 | | Pickwick v Wanderers | Pickwick Cricket Club, Bridgetown | Results |
| 07 Aug 1905 | | Barbados Garrison v Wanderers | The Savannah, St Ann's Garrison | Results |
| 12 Aug 1905 | | Harrison College v Wanderers | Harrison College Ground, Bridgetown | Results |
| 12 Aug 1905 | | Spartan v Lodge School | Spartan Cricket Club Ground, Belleville | Results |
| 17 Aug 1905 | | Wanderers v Barbados Garrison | The Bay, Bridgetown | Results |
| 19 Aug 1905 | | Barbados Garrison v Harrison College | The Savannah, St Ann's Garrison | Results |
| 19 Aug 1905 | | Pickwick v Spartan | Pickwick Cricket Club, Bridgetown | Results |
| 19 Aug 1905 | | Wanderers v Lodge School | The Bay, Bridgetown | Results |
| 26 Aug 1905 | | Spartan v Barbados Garrison | Spartan Cricket Club Ground, Belleville | Results |
| 26 Aug 1905 | | Spartan v Harrison College | Spartan Cricket Club Ground, Belleville | Results |
| 02 Sep 1905 | | Barbados Garrison v Pickwick | The Savannah, St Ann's Garrison | Results |
| 02 Sep 1905 | | Spartan v Wanderers | Spartan Cricket Club Ground, Belleville | Results |
| 23 Sep 1905 | | Spartan v Barbados Garrison | Spartan Cricket Club Ground, Belleville | Results |
| 23 Sep 1905 | | Wanderers v Pickwick | The Bay, Bridgetown | Results |
| 28 Sep 1905 | | Wanderers v Barbados Garrison | The Bay, Bridgetown | Results |
| 30 Sep 1905 | | Harrison College v Barbados Garrison | Harrison College Ground, Bridgetown | Results |
| 30 Sep 1905 | | Lodge School v Wanderers | The Lodge School, Society | Results |
| 30 Sep 1905 | | Spartan v Pickwick | Spartan Cricket Club Ground, Belleville | Results |
| 02 Oct 1905 | | Barbados Garrison v Spartan | The Savannah, St Ann's Garrison | Results |
| 07 Oct 1905 | | Lodge School v Spartan | The Lodge School, Society | Results |
| 07 Oct 1905 | | Pickwick v Barbados Garrison | Pickwick Cricket Club, Bridgetown | Results |
| 14 Oct 1905 | | Harrison College v Pickwick | Harrison College Ground, Bridgetown | Results |
| 14 Oct 1905 | | Wanderers v Spartan | The Bay, Bridgetown | Results |
| 21 Oct 1905 | | Barbados Garrison v Wanderers | The Savannah, St Ann's Garrison | Results |
| 21 Oct 1905 | | Pickwick v Lodge School | Pickwick Cricket Club, Bridgetown | Results |
| 21 Oct 1905 | | Spartan v Harrison College | Spartan Cricket Club Ground, Belleville | Results |
| 28 Oct 1905 | | Barbados Garrison v Lodge School | The Savannah, St Ann's Garrison | Results |
| 28 Oct 1905 | | Wanderers v Harrison College | The Bay, Bridgetown | Results |
| 04 Nov 1905 | | Pickwick v Barbados Garrison | Pickwick Cricket Club, Bridgetown | Results |
| 04 Nov 1905 | | Wanderers v Lodge School | The Bay, Bridgetown | Results |
| 11 Nov 1905 | | Barbados Garrison v Pickwick | The Savannah, St Ann's Garrison | Results |
| 11 Nov 1905 | | Harrison College v Spartan | Harrison College Ground, Bridgetown | Results |
| 11 Nov 1905 | | Wanderers v Pickwick | The Bay, Bridgetown | Results |
| 18 Nov 1905 | | Barbados Garrison v Harrison College | The Savannah, St Ann's Garrison | Results |
| 18 Nov 1905 | | Pickwick v Wanderers | Pickwick Cricket Club, Bridgetown | Results |
| 18 Nov 1905 | | Spartan v Lodge School | Spartan Cricket Club Ground, Belleville | Results |
| 25 Nov 1905 | | Lodge School v Pickwick | The Lodge School, Society | Results |
| 25 Nov 1905 | | Spartan v Wanderers | Spartan Cricket Club Ground, Belleville | Results |
| 25 Nov 1905 | | Wanderers v Spartan | The Bay, Bridgetown | Results |
| 02 Dec 1905 | | Barbados Garrison v Lodge School | The Savannah, St Ann's Garrison | Results |
| 02 Dec 1905 | | Pickwick v Harrison College | Pickwick Cricket Club, Bridgetown | Results |
| 09 Dec 1905 | | Harrison College v Wanderers | Harrison College Ground, Bridgetown | Results |
| 16 Dec 1905 | | Harrison College v Spartan | Harrison College Ground, Bridgetown | Results |
| 23 Dec 1905 | | Lodge School v Pickwick | The Lodge School, Society | Results |
| 06 Jan 1906 | | Pickwick v Spartan | Pickwick Cricket Club, Bridgetown | Results |
| 20 Jan 1906 | | Harrison College v Barbados Garrison | Harrison College Ground, Bridgetown | Results |
| 27 Jan 1906 | | Lodge School v Spartan | The Lodge School, Society | Results |
| 03 Feb 1906 | | Harrison College v Pickwick | Harrison College Ground, Bridgetown | Results |
| 03 Feb 1906 | | Lodge School v Barbados Garrison | The Lodge School, Society | Results |
| 17 Feb 1906 | | Harrison College v Lodge School | Harrison College Ground, Bridgetown | Results |
| 17 Feb 1906 | | Spartan v Pickwick | Spartan Cricket Club Ground, Belleville | Results |
| 24 Feb 1906 | | Lodge School v Harrison College | The Lodge School, Society | Results |
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