| 07 May 2000 | | Sri Lanka v Englewood | Staten Island Psychiatric Center, Staten Island | Results |
| 07 May 2000 | | Lions United v Stars United | Breezy Point, Rockaway | Results |
| 07 May 2000 | | Staten Island Cricket Club v Suburbia | Walker Park, Staten Island | Results |
| 07 May 2000 | | Sportsman v Villagers Pacesetters Sports Athletic Club B | Sportsman Oval, Poughkeepsie | Results |
| 14 May 2000 | | Villagers Pacesetters Sports Athletic Club B v Englewood | Floyd Bennett Field, Brooklyn | Results |
| 14 May 2000 | | Sri Lanka v Stars United | Staten Island Psychiatric Center, Staten Island | Results |
| 14 May 2000 | | Sportsman v Staten Island Cricket Club | Sportsman Oval, Poughkeepsie | Results |
| 21 May 2000 | | Villagers Pacesetters Sports Athletic Club B v Lions United | Floyd Bennett Field No 2, Brooklyn | Results |
| 21 May 2000 | | Sri Lanka v Staten Island Cricket Club | Walker Park, Staten Island | Results |
| 21 May 2000 | | Suburbia v Stars United | not known | Results |
| 21 May 2000 | | Sportsman v Englewood | not known | Results |
| 04 Jun 2000 | | Lions United v Englewood | Breezy Point, Rockaway | Results |
| 04 Jun 2000 | | Staten Island Cricket Club v Sportsman | Walker Park, Staten Island | Results |
| 04 Jun 2000 | | Villagers Pacesetters Sports Athletic Club B v Suburbia | Floyd Bennett Field No 3, Brooklyn | Results |
| 04 Jun 2000 | | Stars United v Sri Lanka | not known | Results |
| 11 Jun 2000 | | Stars United v Sportsman | Staten Island Psychiatric Center, Staten Island | Results |
| 11 Jun 2000 | | Suburbia v Englewood | Roy Wilkins Park, St Albans | Results |
| 11 Jun 2000 | | Lions United v Staten Island Cricket Club | Breezy Point, Rockaway | Results |
| 18 Jun 2000 | | Staten Island Cricket Club v Englewood | Walker Park, Staten Island | Results |
| 18 Jun 2000 | | Lions United v Sri Lanka | Breezy Point, Rockaway | Results |
| 18 Jun 2000 | | Suburbia v Sportsman | Roy Wilkins Park, St Albans | Results |
| 18 Jun 2000 | | Stars United v Villagers Pacesetters Sports Athletic Club B | not known | Results |
| 25 Jun 2000 | | Suburbia v Lions United | Roy Wilkins Park, St Albans | Results |
| 25 Jun 2000 | | Sri Lanka v Sportsman | Staten Island Psychiatric Center, Staten Island | Results |
| 25 Jun 2000 | | Englewood v Stars United | not known | Results |
| 25 Jun 2000 | | Villagers Pacesetters Sports Athletic Club B v Staten Island Cricket Club | Floyd Bennett Field No 4, Brooklyn | Results |
| 02 Jul 2000 | | Sri Lanka v Villagers Pacesetters Sports Athletic Club B | Staten Island Psychiatric Center, Staten Island | Results |
| 02 Jul 2000 | | Lions United v Staten Island Cricket Club | not known | Results |
| 09 Jul 2000 | | Stars United v Staten Island Cricket Club | Staten Island Psychiatric Center, Staten Island | Results |
| 09 Jul 2000 | | Sri Lanka v Suburbia | not known | Results |
| 16 Jul 2000 | | Englewood v Lions United | Denning Park, Englewood | Results |
| 16 Jul 2000 | | Suburbia v Villagers Pacesetters Sports Athletic Club B | Roy Wilkins Park, St Albans | Results |
| 23 Jul 2000 | | Staten Island Cricket Club v Sri Lanka | Walker Park, Staten Island | Results |
| 23 Jul 2000 | | Englewood v Sportsman | Denning Park, Englewood | Results |
| 23 Jul 2000 | | Stars United v Suburbia | East Side Park, Paterson | Results |
| 23 Jul 2000 | | Lions United v Villagers Pacesetters Sports Athletic Club B | Breezy Point, Rockaway | Results |
| 30 Jul 2000 | | Villagers Pacesetters Sports Athletic Club B v Sportsman | Marine Park, Mill Creek | Results |
| 30 Jul 2000 | | Stars United v Lions United | not known | Results |
| 30 Jul 2000 | | Englewood v Sri Lanka | Denning Park, Englewood | Results |
| 06 Aug 2000 | | Englewood v Suburbia | Denning Park, Englewood | Results |
| 06 Aug 2000 | | Stars United v Sportsman | not known | Results |
| 06 Aug 2000 | | Villagers Pacesetters Sports Athletic Club B v Sri Lanka | not known | Results |
| 13 Aug 2000 | | Lions United v Sri Lanka | Breezy Point, Rockaway | Results |
| 13 Aug 2000 | | Englewood v Staten Island Cricket Club | Denning Park, Englewood | Results |
| 13 Aug 2000 | | Sportsman v Suburbia | Sportsman Oval, Poughkeepsie | Results |
| 13 Aug 2000 | | Villagers Pacesetters Sports Athletic Club B v Stars United | not known | Results |
| 20 Aug 2000 | | Lions United v Suburbia | Breezy Point, Rockaway | Results |
| 20 Aug 2000 | | Staten Island Cricket Club v Villagers Pacesetters Sports Athletic Club B | Walker Park, Staten Island | Results |
| 20 Aug 2000 | | Stars United v Englewood | not known | Results |
| 27 Aug 2000 | | Lions United v Sportsman | Breezy Point, Rockaway | Results |
| 27 Aug 2000 | | Staten Island Cricket Club v Stars United | Walker Park, Staten Island | Results |
| 27 Aug 2000 | | Englewood v Villagers Pacesetters Sports Athletic Club B | not known | Results |
| 27 Aug 2000 | | Suburbia v Sri Lanka | Roy Wilkins Park, St Albans | Results |
| 03 Sep 2000 | | Sportsman v Sri Lanka | Sportsman Oval, Poughkeepsie | Results |
| 03 Sep 2000 | | Suburbia v Staten Island Cricket Club | Roy Wilkins Park, St Albans | Results |
| 09 Jul 2000 | | Sportsman v Lions United | Breezy Point, Rockaway | Results |
| 17 Sep 2000 | Semi-Final | Sportsman v not known | not known | Results |
| 17 Sep 2000 | Semi-Final | Lions United v not known | not known | Results |
| 24 Sep 2000 | Final | Sportsman v Lions United | not known | Results |
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