| 31 May 1919 | | Bensonhurst Field Club v Bensonhurst Rovers | Ulmer Park, Brooklyn | Results |
| 30 May 1919 | | Bensonhurst Field Club v Manor Field | Ulmer Park, Brooklyn | Results |
| 30 May 1919 | | Columbia Oval v Columbia Oval Rovers | Pelham Bay Park, Brooklyn | Results |
| 30 May 1919 | | Staten Island Cricket Club v Bensonhurst Rovers | Walker Park, Staten Island | Results |
| 31 May 1919 | | Columbia Oval v Manor Field | Pelham Bay Park, Brooklyn | Results |
| 31 May 1919 | | Staten Island Cricket Club v Columbia Oval Rovers | Walker Park, Staten Island | Results |
| 07 Jun 1919 | | Bensonhurst Rovers v Columbia Oval | Ulmer Park, Brooklyn | Results |
| 14 Jun 1919 | | Bensonhurst Rovers v Columbia Oval Rovers | Ulmer Park, Brooklyn | Results |
| 14 Jun 1919 | | Columbia Oval v Bensonhurst Field Club | Pelham Bay Park, Brooklyn | Results |
| 14 Jun 1919 | | Manor Field v Staten Island Cricket Club | West New Brighton, Staten Island | Results |
| 28 Jun 1919 | | Bensonhurst Field Club v Columbia Oval Rovers | Ulmer Park, Brooklyn | Results |
| 28 Jun 1919 | | Staten Island Cricket Club v Manor Field | Walker Park, Staten Island | Results |
| 04 Jul 1919 | | Bensonhurst Rovers v Columbia Oval Rovers | Ulmer Park, Brooklyn | Results |
| 04 Jul 1919 | | Manor Field v Columbia Oval | West New Brighton, Staten Island | Results |
| 04 Jul 1919 | | Staten Island Cricket Club v Bensonhurst Field Club | Walker Park, Staten Island | Results |
| 05 Jul 1919 | | Columbia Oval Rovers v Bensonhurst Field Club | Crescent Athletic Club Ground, Bay Ridge | Results |
| 05 Jul 1919 | | Manor Field v Bensonhurst Rovers | West New Brighton, Staten Island | Results |
| 05 Jul 1919 | | Staten Island Cricket Club v Columbia Oval | Walker Park, Staten Island | Results |
| 12 Jul 1919 | | Bensonhurst Field Club v Staten Island Cricket Club | Ulmer Park, Brooklyn | Results |
| 12 Jul 1919 | | Columbia Oval v Bensonhurst Rovers | Pelham Bay Park, Brooklyn | Results |
| 12 Jul 1919 | | Manor Field v Columbia Oval Rovers | West New Brighton, Staten Island | Results |
| 19 Jul 1919 | | Bensonhurst Field Club v Manor Field | Ulmer Park, Brooklyn | Results |
| 19 Jul 1919 | | Columbia Oval Rovers v Columbia Oval | Crescent Athletic Club Ground, Bay Ridge | Results |
| 19 Jul 1919 | | Staten Island Cricket Club v Bensonhurst Rovers | Walker Park, Staten Island | Results |
| 26 Jul 1919 | | Bensonhurst Rovers v Bensonhurst Field Club | Ulmer Park, Brooklyn | Results |
| 26 Jul 1919 | | Columbia Oval Rovers v Manor Field | Crescent Athletic Club Ground, Bay Ridge | Results |
| 26 Jul 1919 | | Staten Island Cricket Club v Columbia Oval | Walker Park, Staten Island | Results |
| 02 Aug 1919 | | Bensonhurst Field Club v Columbia Oval | Ulmer Park, Brooklyn | Results |
| 02 Aug 1919 | | Columbia Oval Rovers v Staten Island Cricket Club | Crescent Athletic Club Ground, Bay Ridge | Results |
| 02 Aug 1919 | | Manor Field v Bensonhurst Rovers | West New Brighton, Staten Island | Results |
| 09 Aug 1919 | | Bensonhurst Field Club v Staten Island Cricket Club | Ulmer Park, Brooklyn | Results |
| 09 Aug 1919 | | Columbia Oval v Bensonhurst Rovers | Pelham Bay Park, Brooklyn | Results |
| 09 Aug 1919 | | Manor Field v Columbia Oval Rovers | West New Brighton, Staten Island | Results |
| 16 Aug 1919 | | Bensonhurst Rovers v Manor Field | Ulmer Park, Brooklyn | Results |
| 16 Aug 1919 | | Columbia Oval Rovers v Bensonhurst Field Club | Crescent Athletic Club Ground, Bay Ridge | Results |
| 16 Aug 1919 | | Staten Island Cricket Club v Columbia Oval | Walker Park, Staten Island | Results |
| 23 Aug 1919 | | Bensonhurst Rovers v Columbia Oval Rovers | Ulmer Park, Brooklyn | Results |
| 23 Aug 1919 | | Columbia Oval v Bensonhurst Field Club | Pelham Bay Park, Brooklyn | Results |
| 23 Aug 1919 | | Staten Island Cricket Club v Manor Field | Walker Park, Staten Island | Results |
| 30 Aug 1919 | | Bensonhurst Rovers v Staten Island Cricket Club | Ulmer Park, Brooklyn | Results |
| 30 Aug 1919 | | Columbia Oval v Columbia Oval Rovers | Pelham Bay Park, Brooklyn | Results |
| 30 Aug 1919 | | Manor Field v Bensonhurst Field Club | West New Brighton, Staten Island | Results |
| 02 Sep 1919 | | Bensonhurst Field Club v Bensonhurst Rovers | Ulmer Park, Brooklyn | Results |
| 02 Sep 1919 | | Manor Field v Columbia Oval | West New Brighton, Staten Island | Results |
| 02 Sep 1919 | | Staten Island Cricket Club v Columbia Oval Rovers | Walker Park, Staten Island | Results |
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