| 12 Nov 1999 | Group A | Bloomfield Cricket and Athletic Club v Matara Sports Club | Bloomfield Cricket and Athletic Club Ground, Colombo | Results |
| 12 Nov 1999 | Group A | Burgher Recreation Club v Sebastianites Cricket and Athletic Club | Burgher Recreation Club Ground, Colombo | Results |
| 12 Nov 1999 | Group B | Galle Cricket Club v Tamil Union Cricket and Athletic Club | The Esplanade, Galle | Results |
| 12 Nov 1999 | Group B | Moors Sports Club v Panadura Sports Club | Moors Sports Club Ground, Colombo | Results |
| 12 Nov 1999 | Group A | Nondescripts Cricket Club v Singha Sports Club | Nondescripts Cricket Club Ground, Colombo | Results |
| 12 Nov 1999 | Group B | Police Sports Club v Colts Cricket Club | Police Park Ground, Colombo | Results |
| 12 Nov 1999 | Group B | Sinhalese Sports Club v Antonians Sports Club | Sinhalese Sports Club Ground, Colombo | Results |
| 13 Nov 1999 | Group A | Colombo Cricket Club v Kurunegala Youth Cricket Club | Colombo Cricket Club Ground, Colombo | Results |
| 19 Nov 1999 | Group A | Bloomfield Cricket and Athletic Club v Burgher Recreation Club | Bloomfield Cricket and Athletic Club Ground, Colombo | Results |
| 19 Nov 1999 | Group A | Colombo Cricket Club v Matara Sports Club | Colombo Cricket Club Ground, Colombo | Results |
| 19 Nov 1999 | Group B | Colts Cricket Club v Panadura Sports Club | Colts Cricket Club Ground, Colombo | Results |
| 19 Nov 1999 | Group B | Moors Sports Club v Galle Cricket Club | Moors Sports Club Ground, Colombo | Results |
| 19 Nov 1999 | Group A | Nondescripts Cricket Club v Kurunegala Youth Cricket Club | Nondescripts Cricket Club Ground, Colombo | Results |
| 19 Nov 1999 | Group B | Sinhalese Sports Club v Police Sports Club | Sinhalese Sports Club Ground, Colombo | Results |
| 19 Nov 1999 | Group B | Tamil Union Cricket and Athletic Club v Antonians Sports Club | P Sara Oval, Colombo | Results |
| 20 Nov 1999 | Group A | Sebastianites Cricket and Athletic Club v Singha Sports Club | St Sebastian's College Ground, Moratuwa | Results |
| 26 Nov 1999 | Group A | Burgher Recreation Club v Singha Sports Club | Burgher Recreation Club Ground, Colombo | Results |
| 26 Nov 1999 | Group A | Colombo Cricket Club v Bloomfield Cricket and Athletic Club | Colombo Cricket Club Ground, Colombo | Results |
| 26 Nov 1999 | Group B | Colts Cricket Club v Sinhalese Sports Club | Colts Cricket Club Ground, Colombo | Results |
| 26 Nov 1999 | Group B | Galle Cricket Club v Panadura Sports Club | The Esplanade, Galle | Results |
| 26 Nov 1999 | Group A | Kurunegala Youth Cricket Club v Sebastianites Cricket and Athletic Club | Welagedara Stadium, Kurunegala | Results |
| 26 Nov 1999 | Group B | Moors Sports Club v Antonians Sports Club | Moors Sports Club Ground, Colombo | Results |
| 26 Nov 1999 | Group A | Nondescripts Cricket Club v Matara Sports Club | Nondescripts Cricket Club Ground, Colombo | Results |
| 26 Nov 1999 | Group B | Tamil Union Cricket and Athletic Club v Police Sports Club | P Sara Oval, Colombo | Results |
| 03 Dec 1999 | Group A | Bloomfield Cricket and Athletic Club v Nondescripts Cricket Club | Bloomfield Cricket and Athletic Club Ground, Colombo | Results |
| 03 Dec 1999 | Group A | Burgher Recreation Club v Kurunegala Youth Cricket Club | Burgher Recreation Club Ground, Colombo | Results |
| 03 Dec 1999 | Group A | Colombo Cricket Club v Singha Sports Club | Colombo Cricket Club Ground, Colombo | Results |
| 03 Dec 1999 | Group B | Galle Cricket Club v Sinhalese Sports Club | The Esplanade, Galle | Results |
| 03 Dec 1999 | Group A | Matara Sports Club v Sebastianites Cricket and Athletic Club | Colts Cricket Club Ground, Colombo | Results |
| 03 Dec 1999 | Group B | Moors Sports Club v Police Sports Club | Moors Sports Club Ground, Colombo | Results |
| 03 Dec 1999 | Group B | Panadura Sports Club v Antonians Sports Club | Panadura Esplanade, Panadura | Results |
| 03 Dec 1999 | Group B | Tamil Union Cricket and Athletic Club v Colts Cricket Club | P Sara Oval, Colombo | Results |
| 10 Dec 1999 | Group A | Bloomfield Cricket and Athletic Club v Sebastianites Cricket and Athletic Club | Bloomfield Cricket and Athletic Club Ground, Colombo | Results |
| 10 Dec 1999 | Group A | Burgher Recreation Club v Matara Sports Club | Burgher Recreation Club Ground, Colombo | Results |
| 10 Dec 1999 | Group B | Colts Cricket Club v Moors Sports Club | Colts Cricket Club Ground, Colombo | Results |
| 10 Dec 1999 | Group B | Galle Cricket Club v Antonians Sports Club | The Esplanade, Galle | Results |
| 10 Dec 1999 | Group A | Kurunegala Youth Cricket Club v Singha Sports Club | Welagedara Stadium, Kurunegala | Results |
| 10 Dec 1999 | Group A | Nondescripts Cricket Club v Colombo Cricket Club | Nondescripts Cricket Club Ground, Colombo | Results |
| 10 Dec 1999 | Group B | Panadura Sports Club v Police Sports Club | Panadura Esplanade, Panadura | Results |
| 10 Dec 1999 | Group B | Sinhalese Sports Club v Tamil Union Cricket and Athletic Club | Sinhalese Sports Club Ground, Colombo | Results |
| 17 Dec 1999 | Group A | Colombo Cricket Club v Sebastianites Cricket and Athletic Club | Colombo Cricket Club Ground, Colombo | Results |
| 17 Dec 1999 | Group B | Colts Cricket Club v Antonians Sports Club | Colts Cricket Club Ground, Colombo | Results |
| 17 Dec 1999 | Group A | Kurunegala Youth Cricket Club v Bloomfield Cricket and Athletic Club | Welagedara Stadium, Kurunegala | Results |
| 17 Dec 1999 | Group A | Matara Sports Club v Singha Sports Club | The Esplanade, Galle | Results |
| 17 Dec 1999 | Group A | Nondescripts Cricket Club v Burgher Recreation Club | Nondescripts Cricket Club Ground, Colombo | Results |
| 17 Dec 1999 | Group B | Panadura Sports Club v Tamil Union Cricket and Athletic Club | Panadura Esplanade, Panadura | Results |
| 17 Dec 1999 | Group B | Sinhalese Sports Club v Moors Sports Club | Sinhalese Sports Club Ground, Colombo | Results |
| 26 Dec 1999 | Group A | Bloomfield Cricket and Athletic Club v Singha Sports Club | Bloomfield Cricket and Athletic Club Ground, Colombo | Results |
| 26 Dec 1999 | Group A | Burgher Recreation Club v Colombo Cricket Club | Burgher Recreation Club Ground, Colombo | Results |
| 26 Dec 1999 | Group B | Colts Cricket Club v Galle Cricket Club | Colts Cricket Club Ground, Colombo | Results |
| 26 Dec 1999 | Group A | Kurunegala Youth Cricket Club v Matara Sports Club | Welagedara Stadium, Kurunegala | Results |
| 26 Dec 1999 | Group A | Nondescripts Cricket Club v Sebastianites Cricket and Athletic Club | Nondescripts Cricket Club Ground, Colombo | Results |
| 26 Dec 1999 | Group B | Panadura Sports Club v Sinhalese Sports Club | Panadura Esplanade, Panadura | Results |
| 26 Dec 1999 | Group B | Police Sports Club v Antonians Sports Club | Police Park Ground, Colombo | Results |
| 26 Dec 1999 | Group B | Tamil Union Cricket and Athletic Club v Moors Sports Club | P Sara Oval, Colombo | Results |
| 02 Jan 2000 | Group B | Police Sports Club v Galle Cricket Club | Police Park Ground, Colombo | Results |
| 29 Jan 2000 | Plate | Bloomfield Cricket and Athletic Club v Panadura Sports Club | Bloomfield Cricket and Athletic Club Ground, Colombo | Results |
| 29 Jan 2000 | Super League | Burgher Recreation Club v Moors Sports Club | Burgher Recreation Club Ground, Colombo | Results |
| 29 Jan 2000 | Super League | Colombo Cricket Club v Tamil Union Cricket and Athletic Club | Colombo Cricket Club Ground, Colombo | Results |
| 29 Jan 2000 | Super League | Colts Cricket Club v Kurunegala Youth Cricket Club | Colts Cricket Club Ground, Colombo | Results |
| 29 Jan 2000 | Plate | Galle Cricket Club v Singha Sports Club | The Esplanade, Galle | Results |
| 29 Jan 2000 | Plate | Matara Sports Club v Police Sports Club | Uyanwatte Stadium, Matara | Results |
| 29 Jan 2000 | Plate | Nondescripts Cricket Club v Antonians Sports Club | Nondescripts Cricket Club Ground, Colombo | Results |
| 29 Jan 2000 | Super League | Sinhalese Sports Club v Sebastianites Cricket and Athletic Club | Sinhalese Sports Club Ground, Colombo | Results |
| 04 Feb 2000 | Plate | Bloomfield Cricket and Athletic Club v Antonians Sports Club | Bloomfield Cricket and Athletic Club Ground, Colombo | Results |
| 04 Feb 2000 | Super League | Colombo Cricket Club v Moors Sports Club | Nondescripts Cricket Club Ground, Colombo | Results |
| 04 Feb 2000 | Super League | Colts Cricket Club v Sebastianites Cricket and Athletic Club | Colts Cricket Club Ground, Colombo | Results |
| 04 Feb 2000 | Plate | Matara Sports Club v Galle Cricket Club | Uyanwatte Stadium, Matara | Results |
| 04 Feb 2000 | Plate | Panadura Sports Club v Nondescripts Cricket Club | Panadura Esplanade, Panadura | Results |
| 04 Feb 2000 | Super League | Sinhalese Sports Club v Kurunegala Youth Cricket Club | Sinhalese Sports Club Ground, Colombo | Results |
| 04 Feb 2000 | Super League | Tamil Union Cricket and Athletic Club v Burgher Recreation Club | P Sara Oval, Colombo | Results |
| 06 Feb 2000 | Plate | Police Sports Club v Singha Sports Club | Police Park Ground, Colombo | Results |
| 11 Feb 2000 | Plate | Bloomfield Cricket and Athletic Club v Galle Cricket Club | Bloomfield Cricket and Athletic Club Ground, Colombo | Results |
| 11 Feb 2000 | Super League | Burgher Recreation Club v Sinhalese Sports Club | Burgher Recreation Club Ground, Colombo | Results |
| 11 Feb 2000 | Super League | Colombo Cricket Club v Colts Cricket Club | Colombo Cricket Club Ground, Colombo | Results |
| 11 Feb 2000 | Super League | Kurunegala Youth Cricket Club v Tamil Union Cricket and Athletic Club | Welagedara Stadium, Kurunegala | Results |
| 11 Feb 2000 | Plate | Matara Sports Club v Antonians Sports Club | Uyanwatte Stadium, Matara | Results |
| 11 Feb 2000 | Super League | Moors Sports Club v Sebastianites Cricket and Athletic Club | Moors Sports Club Ground, Colombo | Results |
| 11 Feb 2000 | Plate | Panadura Sports Club v Singha Sports Club | Panadura Esplanade, Panadura | Results |
| 11 Feb 2000 | Plate | Police Sports Club v Nondescripts Cricket Club | Police Park Ground, Colombo | Results |
| 18 Feb 2000 | Plate | Antonians Sports Club v Singha Sports Club | de Mazenod College Ground, Kandana | Results |
| 18 Feb 2000 | Super League | Burgher Recreation Club v Colts Cricket Club | Burgher Recreation Club Ground, Colombo | Results |
| 18 Feb 2000 | Super League | Moors Sports Club v Kurunegala Youth Cricket Club | Moors Sports Club Ground, Colombo | Results |
| 18 Feb 2000 | Plate | Nondescripts Cricket Club v Galle Cricket Club | Nondescripts Cricket Club Ground, Colombo | Results |
| 18 Feb 2000 | Plate | Panadura Sports Club v Matara Sports Club | Panadura Esplanade, Panadura | Results |
| 18 Feb 2000 | Plate | Police Sports Club v Bloomfield Cricket and Athletic Club | Police Park Ground, Colombo | Results |
| 18 Feb 2000 | Super League | Sinhalese Sports Club v Colombo Cricket Club | Sinhalese Sports Club Ground, Colombo | Results |
| 18 Feb 2000 | Super League | Tamil Union Cricket and Athletic Club v Sebastianites Cricket and Athletic Club | P Sara Oval, Colombo | Results |
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