| 23 May 1914 | | United Shoe Machinery, Beverly v Athletics | McKay Street Athletic Park, Beverly | Results |
| 13 Jun 1914 | | United Shoe Machinery, Beverly v United Shoe Machinery, Beverly Blues | McKay Street Athletic Park, Beverly | Results |
| 11 Jul 1914 | | United Shoe Machinery, Beverly v Brockton | McKay Street Athletic Park, Beverly | Results |
| 27 Jun 1914 | | United Shoe Machinery, Beverly v Canton | McKay Street Athletic Park, Beverly | Results |
| 01 Aug 1914 | | United Shoe Machinery, Beverly v Caribbean | McKay Street Athletic Park, Beverly | Results |
| 15 Aug 1914 | | United Shoe Machinery, Beverly v Everett | McKay Street Athletic Park, Beverly | Results |
| 26 Sep 1914 | | United Shoe Machinery, Beverly v Lawrence | McKay Street Athletic Park, Beverly | Results |
| 29 Aug 1914 | | United Shoe Machinery, Beverly v Needham | McKay Street Athletic Park, Beverly | Results |
| 19 Sep 1914 | | United Shoe Machinery, Beverly v West Indian Wanderers | McKay Street Athletic Park, Beverly | Results |
| 12 Sep 1914 | | United Shoe Machinery, Beverly Blues v Athletics | McKay Street Athletic Park, Beverly | Results |
| 22 Aug 1914 | | United Shoe Machinery, Beverly Blues v United Shoe Machinery, Beverly | McKay Street Athletic Park, Beverly | Results |
| 06 Jun 1914 | | United Shoe Machinery, Beverly Blues v Canton | McKay Street Athletic Park, Beverly | Results |
| 18 Jul 1914 | | United Shoe Machinery, Beverly Blues v Caribbean | McKay Street Athletic Park, Beverly | Results |
| 05 Sep 1914 | | United Shoe Machinery, Beverly Blues v Everett | McKay Street Athletic Park, Beverly | Results |
| 20 Jun 1914 | | United Shoe Machinery, Beverly Blues v Lawrence | McKay Street Athletic Park, Beverly | Results |
| 25 Jul 1914 | | United Shoe Machinery, Beverly Blues v St George's Club of Boston | McKay Street Athletic Park, Beverly | Results |
| 16 May 1914 | | United Shoe Machinery, Beverly Blues v Standard | McKay Street Athletic Park, Beverly | Results |
| 08 Aug 1914 | | United Shoe Machinery, Beverly Blues v West Indian Wanderers | McKay Street Athletic Park, Beverly | Results |
| 01 Aug 1914 | | Brockton v Athletics | Cross Street, Brockton | Results |
| 12 Sep 1914 | | Brockton v United Shoe Machinery, Beverly | Cross Street, Brockton | Results |
| 25 Jul 1914 | | Brockton v Canton | Cross Street, Brockton | Results |
| 23 May 1914 | | Brockton v Everett | Cross Street, Brockton | Results |
| 18 Jul 1914 | | Brockton v Lawrence | Cross Street, Brockton | Results |
| 27 Jun 1914 | | Brockton v Needham | Cross Street, Brockton | Results |
| 22 Aug 1914 | | Brockton v St George's Club of Boston | Cross Street, Brockton | Results |
| 06 Jun 1914 | | Brockton v Standard | Cross Street, Brockton | Results |
| 29 Aug 1914 | | Brockton v West Indian Wanderers | Cross Street, Brockton | Results |
| 18 Jul 1914 | | Canton v Athletics | Norfolk Street, Canton | Results |
| 05 Sep 1914 | | Canton v United Shoe Machinery, Beverly | Norfolk Street, Canton | Results |
| 15 Aug 1914 | | United Shoe Machinery, Beverly Blues v Canton | McKay Street Athletic Park, Beverly | Results |
| 26 Sep 1914 | | Canton v Brockton | Norfolk Street, Canton | Results |
| 23 May 1914 | | Canton v Caribbean | Norfolk Street, Canton | Results |
| 13 Jun 1914 | | Canton v Everett | Norfolk Street, Canton | Results |
| 01 Aug 1914 | | Canton v Needham | Norfolk Street, Canton | Results |
| 20 Jun 1914 | | Canton v St George's Club of Boston | Norfolk Street, Canton | Results |
| 11 Jul 1914 | | Canton v Standard | Norfolk Street, Canton | Results |
| 06 Jun 1914 | | Everett v United Shoe Machinery, Beverly | Corbett Park, Everett | Results |
| 27 Jun 1914 | | Everett v United Shoe Machinery, Beverly Blues | Corbett Park, Everett | Results |
| 08 Aug 1914 | | Everett v Brockton | Corbett Park, Everett | Results |
| 22 Aug 1914 | | Everett v Canton | Corbett Park, Everett | Results |
| 20 Jun 1914 | | Everett v Caribbean | Corbett Park, Everett | Results |
| 12 Sep 1914 | | Everett v Lawrence | Corbett Park, Everett | Results |
| 19 Sep 1914 | | Everett v Needham | Corbett Park, Everett | Results |
| 16 May 1914 | | Everett v St George's Club of Boston | Corbett Park, Everett | Results |
| 25 Jul 1914 | | Everett v Standard | Corbett Park, Everett | Results |
| 15 Aug 1914 | | Lawrence v Athletics | South Side, Lawrence | Results |
| 25 Jul 1914 | | Lawrence v United Shoe Machinery, Beverly | South Side, Lawrence | Results |
| 29 Aug 1914 | | Lawrence v United Shoe Machinery, Beverly Blues | South Side, Lawrence | Results |
| 19 Sep 1914 | | Lawrence v Brockton | South Side, Lawrence | Results |
| 27 Jun 1914 | | Lawrence v Caribbean | South Side, Lawrence | Results |
| 11 Jul 1914 | | Lawrence v Everett | South Side, Lawrence | Results |
| 13 Jun 1914 | | Lawrence v Needham | South Side, Lawrence | Results |
| 08 Aug 1914 | | Lawrence v St George's Club of Boston | South Side, Lawrence | Results |
| 16 May 1914 | | Lawrence v West Indian Wanderers | South Side, Lawrence | Results |
| 20 Jun 1914 | | Needham v United Shoe Machinery, Beverly | YMCA Ground, Needham | Results |
| 05 Sep 1914 | | Needham v Brockton | YMCA Ground, Needham | Results |
| 16 May 1914 | | Needham v Canton | YMCA Ground, Needham | Results |
| 12 Sep 1914 | | Needham v Caribbean | YMCA Ground, Needham | Results |
| 18 Jul 1914 | | Needham v Everett | YMCA Ground, Needham | Results |
| 22 Aug 1914 | | Needham v Lawrence | YMCA Ground, Needham | Results |
| 06 Jun 1914 | | Needham v St George's Club of Boston | YMCA Ground, Needham | Results |
| 08 Aug 1914 | | Needham v Standard | YMCA Ground, Needham | Results |
| 26 Sep 1914 | | Needham v West Indian Wanderers | YMCA Ground, Needham | Results |
| 05 Sep 1914 | | St George's Club of Boston v Athletics | St George's Cricket Club Ground, Boston | Results |
| 26 Sep 1914 | | St George's Club of Boston v United Shoe Machinery, Beverly Blues | St George's Cricket Club Ground, Boston | Results |
| 13 Jun 1914 | | St George's Club of Boston v Brockton | St George's Cricket Club Ground, Boston | Results |
| 29 Aug 1914 | | St George's Club of Boston v Canton | St George's Cricket Club Ground, Boston | Results |
| 01 Aug 1914 | | St George's Club of Boston v Everett | St George's Cricket Club Ground, Boston | Results |
| 23 May 1914 | | St George's Club of Boston v Lawrence | St George's Cricket Club Ground, Boston | Results |
| 15 Aug 1914 | | St George's Club of Boston v Needham | St George's Cricket Club Ground, Boston | Results |
| 19 Sep 1914 | | St George's Club of Boston v Standard | St George's Cricket Club Ground, Boston | Results |
| 11 Jul 1914 | | West Indian Wanderers v St George's Club of Boston | Franklin Field, Boston | Results |
| 08 Aug 1914 | | Athletics v United Shoe Machinery, Beverly | Franklin Field, Boston | Results |
| 11 Jul 1914 | | Athletics v United Shoe Machinery, Beverly Blues | Franklin Field, Boston | Results |
| 16 May 1914 | | Athletics v Brockton | Franklin Field, Boston | Results |
| 19 Sep 1914 | | Athletics v Canton | Franklin Field, Boston | Results |
| 25 Jul 1914 | | Athletics v Caribbean | Franklin Field, Boston | Results |
| 06 Jun 1914 | | Athletics v Lawrence | Franklin Field, Boston | Results |
| 27 Jun 1914 | | Athletics v St George's Club of Boston | Franklin Field, Boston | Results |
| 29 Aug 1914 | | Athletics v Standard | Franklin Field, Boston | Results |
| 22 Aug 1914 | | Athletics v West Indian Wanderers | Franklin Field, Boston | Results |
| 26 Sep 1914 | | Caribbean v Athletics | Franklin Field, Boston | Results |
| 16 May 1914 | | Caribbean v United Shoe Machinery, Beverly | Franklin Field, Boston | Results |
| 19 Sep 1914 | | Caribbean v United Shoe Machinery, Beverly Blues | Franklin Field, Boston | Results |
| 08 Aug 1914 | | Caribbean v Canton | Franklin Field, Boston | Results |
| 29 Aug 1914 | | Caribbean v Everett | Franklin Field, Boston | Results |
| 05 Sep 1914 | | Caribbean v Lawrence | Franklin Field, Boston | Results |
| 11 Jul 1914 | | Caribbean v Needham | Franklin Field, Boston | Results |
| 22 Aug 1914 | | Caribbean v Standard | Franklin Field, Boston | Results |
| 06 Jun 1914 | | Caribbean v West Indian Wanderers | Franklin Field, Boston | Results |
| 20 Jun 1914 | | Standard v Athletics | Franklin Field, Boston | Results |
| 01 Aug 1914 | | Standard v United Shoe Machinery, Beverly Blues | Franklin Field, Boston | Results |
| 15 Aug 1914 | | Standard v Brockton | Franklin Field, Boston | Results |
| 12 Sep 1914 | | Standard v Canton | Franklin Field, Boston | Results |
| 13 Jun 1914 | | Standard v Caribbean | Franklin Field, Boston | Results |
| 26 Sep 1914 | | Standard v Everett | Franklin Field, Boston | Results |
| 23 May 1914 | | Standard v Needham | Franklin Field, Boston | Results |
| 18 Jul 1914 | | Standard v St George's Club of Boston | Franklin Field, Boston | Results |
| 05 Sep 1914 | | Standard v West Indian Wanderers | Franklin Field, Boston | Results |
| 18 Jul 1914 | | West Indian Wanderers v United Shoe Machinery, Beverly | Franklin Field, Boston | Results |
| 23 May 1914 | | West Indian Wanderers v United Shoe Machinery, Beverly Blues | Franklin Field, Boston | Results |
| 20 Jun 1914 | | West Indian Wanderers v Brockton | Franklin Field, Boston | Results |
| 15 Aug 1914 | | West Indian Wanderers v Caribbean | Franklin Field, Boston | Results |
| 01 Aug 1914 | | West Indian Wanderers v Lawrence | Franklin Field, Boston | Results |
| 25 Jul 1914 | | Needham v West Indian Wanderers | YMCA Ground, Needham | Results |
| 12 Sep 1914 | | West Indian Wanderers v St George's Club of Boston | Franklin Field, Boston | Results |
| 27 Jun 1914 | | West Indian Wanderers v Standard | Franklin Field, Boston | Results |
| 13 Jun 1914 | | West Indian Wanderers v Athletics | Franklin Field, Boston | Results |
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