| 09 Jul 1898 | | Harrison College v Lodge School | Harrison College Ground, Bridgetown | Results |
| 16 Jul 1898 | | Harrison College v Spartan | Harrison College Ground, Bridgetown | Results |
| 23 Jul 1898 | | Harrison College v Leeward | Harrison College Ground, Bridgetown | Results |
| 30 Jul 1898 | | Spartan v Lodge School | Spartan Cricket Club Ground, Belleville | Results |
| 30 Jul 1898 | | Windward v Leeward | Codrington College, St John | Results |
| 06 Aug 1898 | | Harrison College v Windward | Harrison College Ground, Bridgetown | Results |
| 06 Aug 1898 | | Leeward v Lodge School | Hannays Pasture, St Lucy | Results |
| 13 Aug 1898 | | Leeward v Harrison College | Hannays Pasture, St Lucy | Results |
| 13 Aug 1898 | | Spartan v Windward | Spartan Cricket Club Ground, Belleville | Results |
| 13 Aug 1898 | | Wanderers v Lodge School | The Bay, Bridgetown | Results |
| 27 Aug 1898 | | Pickwick v Spartan | Pickwick Cricket Club, Bridgetown | Results |
| 27 Aug 1898 | | Windward v Lodge School | Codrington College, St John | Results |
| 10 Sep 1898 | | Pickwick v Lodge School | Pickwick Cricket Club, Bridgetown | Results |
| 10 Sep 1898 | | Wanderers v Leeward | The Bay, Bridgetown | Results |
| 24 Sep 1898 | | Spartan v Wanderers | Spartan Cricket Club Ground, Belleville | Results |
| 08 Oct 1898 | | Leeward v Pickwick | Hannays Pasture, St Lucy | Results |
| 08 Oct 1898 | | Lodge School v Wanderers | The Lodge School, Society | Results |
| 15 Oct 1898 | | Lodge School v Harrison College | The Lodge School, Society | Results |
| 22 Oct 1898 | | Harrison College v Wanderers | Harrison College Ground, Bridgetown | Results |
| 22 Oct 1898 | | Windward v Pickwick | Codrington College, St John | Results |
| 29 Oct 1898 | | Lodge School v Leeward | Pickwick Cricket Club, Bridgetown | Results |
| 05 Nov 1898 | | Leeward v Spartan | Hannays Pasture, St Lucy | Results |
| 05 Nov 1898 | | Lodge School v Windward | The Lodge School, Society | Results |
| 05 Nov 1898 | | Pickwick v Harrison College | Pickwick Cricket Club, Bridgetown | Results |
| 16 Nov 1898 | | Pickwick v Wanderers | Pickwick Cricket Club, Bridgetown | Results |
| 19 Nov 1898 | | Leeward v Windward | Hannays Pasture, St Lucy | Results |
| 19 Nov 1898 | | Spartan v Harrison College | Spartan Cricket Club Ground, Belleville | Results |
| 03 Dec 1898 | | Spartan v Pickwick | Spartan Cricket Club Ground, Belleville | Results |
| 03 Dec 1898 | | Windward v Harrison College | Codrington College, St John | Results |
| 10 Dec 1898 | | Pickwick v Leeward | Pickwick Cricket Club, Bridgetown | Results |
| 10 Dec 1898 | | Wanderers v Harrison College | The Bay, Bridgetown | Results |
| 17 Dec 1898 | | Harrison College v Pickwick | Harrison College Ground, Bridgetown | Results |
| 17 Dec 1898 | | Wanderers v Windward | The Bay, Bridgetown | Results |
| 31 Dec 1898 | | Windward v Spartan | Codrington College, St John | Results |
| 14 Jan 1899 | | Spartan v Leeward | Spartan Cricket Club Ground, Belleville | Results |
| 14 Jan 1899 | | Windward v Wanderers | Codrington College, St John | Results |
| 28 Jan 1899 | | Lodge School v Spartan | The Lodge School, Society | Results |
| 28 Jan 1899 | | Wanderers v Pickwick | The Bay, Bridgetown | Results |
| 11 Feb 1899 | | Leeward v Wanderers | Hannays Pasture, St Lucy | Results |
| 11 Feb 1899 | | Pickwick v Windward | Pickwick Cricket Club, Bridgetown | Results |
| 25 Feb 1899 | | Lodge School v Pickwick | The Lodge School, Society | Results |
| 25 Feb 1899 | | Wanderers v Spartan | The Bay, Bridgetown | Results |
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