| 03 May 2009 | | Manchester United v International | East Side Park, Paterson | Results |
| 03 May 2009 | | North Province v Englewood | Miller Field, Staten Island | Results |
| 03 May 2009 | | Staten Island Cricket Club v Falcons | Walker Park, Staten Island | Results |
| 03 May 2009 | | Pioneer v Jamaica Ex-Police | Roy Sweeney Oval, Spring Creek | Results |
| 03 May 2009 | | Frank Parson v Unity | Fairmount Park, Philadelphia | Results |
| 10 May 2009 | | Pioneer v Unity | Roy Sweeney Oval, Spring Creek | Results |
| 10 May 2009 | | Manchester United v Jamaica Ex-Police | East Side Park, Paterson | Results |
| 10 May 2009 | | North Province v Falcons | Miller Field, Staten Island | Results |
| 10 May 2009 | | Staten Island Cricket Club v Englewood | Walker Park, Staten Island | Results |
| 10 May 2009 | | International v Frank Parson | Fairmount Park, Philadelphia | Results |
| 17 May 2009 | | Unity v Manchester United | Miller Field, Staten Island | Results |
| 17 May 2009 | | International v Englewood | Papa Playground, Philadelphia | Results |
| 17 May 2009 | | Falcons v Pioneer | Floyd Bennett Field No 4, Brooklyn | Results |
| 17 May 2009 | | Jamaica Ex-Police v Staten Island Cricket Club | Roy Wilkins Park, St Albans | Results |
| 17 May 2009 | | Frank Parson v North Province | Fairmount Park, Philadelphia | Results |
| 31 May 2009 | | Englewood v Unity | Denning Park, Englewood | Results |
| 31 May 2009 | | Manchester United v Frank Parson | East Side Park, Paterson | Results |
| 31 May 2009 | | Jamaica Ex-Police v Falcons | Roy Wilkins Park, St Albans | Results |
| 31 May 2009 | | North Province v Pioneer | Miller Field, Staten Island | Results |
| 31 May 2009 | | International v Staten Island Cricket Club | Fairmount Park, Philadelphia | Results |
| 07 Jun 2009 | | Englewood v Manchester United | Denning Park, Englewood | Results |
| 07 Jun 2009 | | Pioneer v Staten Island Cricket Club | Roy Sweeney Oval, Spring Creek | Results |
| 07 Jun 2009 | | Falcons v International | Floyd Bennett Field No 4, Brooklyn | Results |
| 07 Jun 2009 | | Unity v North Province | Miller Field, Staten Island | Results |
| 07 Jun 2009 | | Frank Parson v Jamaica Ex-Police | Fairmount Park, Philadelphia | Results |
| 13 Jun 2009 | | Englewood v Falcons | Denning Park, Englewood | Results |
| 14 Jun 2009 | | Staten Island Cricket Club v Unity | Walker Park, Staten Island | Results |
| 14 Jun 2009 | | Englewood v Jamaica Ex-Police | Denning Park, Englewood | Results |
| 14 Jun 2009 | | Manchester United v Falcons | East Side Park, Paterson | Results |
| 14 Jun 2009 | | International v North Province | Fairmount Park, Philadelphia | Results |
| 14 Jun 2009 | | Pioneer v Frank Parson | Roy Sweeney Oval, Spring Creek | Results |
| 21 Jun 2009 | | Jamaica Ex-Police v Unity | Roy Wilkins Park, St Albans | Results |
| 21 Jun 2009 | | Staten Island Cricket Club v Frank Parson | Walker Park, Staten Island | Results |
| 21 Jun 2009 | | International v Pioneer | Fairmount Park, Philadelphia | Results |
| 21 Jun 2009 | | North Province v Manchester United | Miller Field, Staten Island | Results |
| 28 Jun 2009 | | Staten Island Cricket Club v Manchester United | Walker Park, Staten Island | Results |
| 28 Jun 2009 | | Pioneer v Englewood | Roy Sweeney Oval, Spring Creek | Results |
| 28 Jun 2009 | | Falcons v Frank Parson | Floyd Bennett Field No 4, Brooklyn | Results |
| 28 Jun 2009 | | International v Unity | Fairmount Park, Philadelphia | Results |
| 28 Jun 2009 | | North Province v Jamaica Ex-Police | Miller Field, Staten Island | Results |
| 12 Jul 2009 | | Englewood v Frank Parson | Denning Park, Englewood | Results |
| 12 Jul 2009 | | Manchester United v Pioneer | East Side Park, Paterson | Results |
| 12 Jul 2009 | | Unity v Falcons | Miller Field, Staten Island | Results |
| 12 Jul 2009 | | Staten Island Cricket Club v North Province | Walker Park, Staten Island | Results |
| 12 Jul 2009 | | Jamaica Ex-Police v International | Roy Wilkins Park, St Albans | Results |
| 19 Jul 2009 | Semi-Final | International v Frank Parson | Fairmount Park, Philadelphia | Results |
| 19 Jul 2009 | Semi-Final | Pioneer v Staten Island Cricket Club | not known | Results |
| 26 Jul 2009 | Final | International v Pioneer | not known | Results |
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