| 22 May 1920 | | Brockton v West Indian Wanderers | Cross Street, Brockton | Results |
| 22 May 1920 | | Everett v St George's Club of Boston | Corbett Park, Everett | Results |
| 22 May 1920 | | Needham v United Shoe Machinery, Beverly | YMCA Ground, Needham | Results |
| 22 May 1920 | | West India Club A v Standard | Franklin Field, Boston | Results |
| 22 May 1920 | | Athletics v West India Club B | Franklin Field, Boston | Results |
| 22 May 1920 | | Caribbean v Spartan | Franklin Field, Boston | Results |
| 29 May 1920 | | Everett v Brockton | Corbett Park, Everett | Results |
| 29 May 1920 | | St George's Club of Boston v Spartan | St George's Cricket Club Ground, Boston | Results |
| 29 May 1920 | | United Shoe Machinery, Beverly v Standard | McKay Street Athletic Park, Beverly | Results |
| 29 May 1920 | | West India Club B v West Indian Wanderers | Franklin Field, Boston | Results |
| 29 May 1920 | | Athletics v West India Club A | Franklin Field, Boston | Results |
| 29 May 1920 | | Caribbean v Needham | Franklin Field, Boston | Results |
| 05 Jun 1920 | | Spartan v Athletics | Franklin Field, Boston | Results |
| 05 Jun 1920 | | St George's Club of Boston v Needham | St George's Cricket Club Ground, Boston | Results |
| 05 Jun 1920 | | United Shoe Machinery, Beverly v Brockton | McKay Street Athletic Park, Beverly | Results |
| 05 Jun 1920 | | West India Club B v Everett | Franklin Field, Boston | Results |
| 05 Jun 1920 | | Standard v Caribbean | Franklin Field, Boston | Results |
| 05 Jun 1920 | | West Indian Wanderers v West India Club A | Franklin Field, Boston | Results |
| 12 Jun 1920 | | Brockton v Caribbean | Cross Street, Brockton | Results |
| 12 Jun 1920 | | Needham v Athletics | YMCA Ground, Needham | Results |
| 12 Jun 1920 | | Spartan v West India Club B | Franklin Field, Boston | Results |
| 12 Jun 1920 | | West India Club A v Everett | Franklin Field, Boston | Results |
| 12 Jun 1920 | | Standard v St George's Club of Boston | Franklin Field, Boston | Results |
| 12 Jun 1920 | | West Indian Wanderers v United Shoe Machinery, Beverly | Franklin Field, Boston | Results |
| 19 Jun 1920 | | Brockton v St George's Club of Boston | Cross Street, Brockton | Results |
| 19 Jun 1920 | | Everett v Spartan | Corbett Park, Everett | Results |
| 19 Jun 1920 | | United Shoe Machinery, Beverly v West India Club A | McKay Street Athletic Park, Beverly | Results |
| 19 Jun 1920 | | West India Club B v Needham | Franklin Field, Boston | Results |
| 19 Jun 1920 | | Athletics v Standard | Franklin Field, Boston | Results |
| 19 Jun 1920 | | Caribbean v West Indian Wanderers | Franklin Field, Boston | Results |
| 26 Jun 1920 | | Needham v Everett | YMCA Ground, Needham | Results |
| 26 Jun 1920 | | Spartan v Standard | Franklin Field, Boston | Results |
| 26 Jun 1920 | | United Shoe Machinery, Beverly v West India Club B | McKay Street Athletic Park, Beverly | Results |
| 26 Jun 1920 | | West India Club A v Caribbean | Franklin Field, Boston | Results |
| 26 Jun 1920 | | Athletics v Brockton | Franklin Field, Boston | Results |
| 26 Jun 1920 | | West Indian Wanderers v St George's Club of Boston | Franklin Field, Boston | Results |
| 17 Jul 1920 | | Spartan v Caribbean | Franklin Field, Boston | Results |
| 17 Jul 1920 | | St George's Club of Boston v Everett | St George's Cricket Club Ground, Boston | Results |
| 17 Jul 1920 | | United Shoe Machinery, Beverly v Needham | McKay Street Athletic Park, Beverly | Results |
| 17 Jul 1920 | | West India Club B v Athletics | Franklin Field, Boston | Results |
| 17 Jul 1920 | | Standard v West India Club A | Franklin Field, Boston | Results |
| 17 Jul 1920 | | West Indian Wanderers v Brockton | Franklin Field, Boston | Results |
| 24 Jul 1920 | | Brockton v Everett | Cross Street, Brockton | Results |
| 24 Jul 1920 | | Needham v Caribbean | YMCA Ground, Needham | Results |
| 24 Jul 1920 | | Spartan v St George's Club of Boston | Franklin Field, Boston | Results |
| 24 Jul 1920 | | West India Club A v Athletics | Franklin Field, Boston | Results |
| 24 Jul 1920 | | Standard v United Shoe Machinery, Beverly | Franklin Field, Boston | Results |
| 24 Jul 1920 | | West Indian Wanderers v West India Club B | Franklin Field, Boston | Results |
| 31 Jul 1920 | | Brockton v United Shoe Machinery, Beverly | Cross Street, Brockton | Results |
| 31 Jul 1920 | | Everett v West India Club B | Corbett Park, Everett | Results |
| 31 Jul 1920 | | Needham v St George's Club of Boston | YMCA Ground, Needham | Results |
| 31 Jul 1920 | | West India Club A v West Indian Wanderers | Franklin Field, Boston | Results |
| 31 Jul 1920 | | Athletics v Spartan | Franklin Field, Boston | Results |
| 31 Jul 1920 | | Caribbean v Standard | Franklin Field, Boston | Results |
| 07 Aug 1920 | | Everett v West India Club A | Corbett Park, Everett | Results |
| 07 Aug 1920 | | St George's Club of Boston v Standard | St George's Cricket Club Ground, Boston | Results |
| 07 Aug 1920 | | United Shoe Machinery, Beverly v West Indian Wanderers | McKay Street Athletic Park, Beverly | Results |
| 07 Aug 1920 | | West India Club B v Spartan | Franklin Field, Boston | Results |
| 07 Aug 1920 | | Athletics v Needham | Franklin Field, Boston | Results |
| 07 Aug 1920 | | Caribbean v Brockton | Franklin Field, Boston | Results |
| 14 Aug 1920 | | Needham v West India Club B | YMCA Ground, Needham | Results |
| 14 Aug 1920 | | Spartan v Needham | Franklin Field, Boston | Results |
| 14 Aug 1920 | | St George's Club of Boston v Brockton | St George's Cricket Club Ground, Boston | Results |
| 14 Aug 1920 | | West India Club A v United Shoe Machinery, Beverly | Franklin Field, Boston | Results |
| 14 Aug 1920 | | Standard v Athletics | Franklin Field, Boston | Results |
| 14 Aug 1920 | | West Indian Wanderers v Caribbean | Franklin Field, Boston | Results |
| 21 Aug 1920 | | Brockton v Athletics | Cross Street, Brockton | Results |
| 21 Aug 1920 | | Everett v Needham | Corbett Park, Everett | Results |
| 21 Aug 1920 | | St George's Club of Boston v West Indian Wanderers | St George's Cricket Club Ground, Boston | Results |
| 21 Aug 1920 | | West India Club B v United Shoe Machinery, Beverly | Franklin Field, Boston | Results |
| 21 Aug 1920 | | Caribbean v West India Club A | Franklin Field, Boston | Results |
| 21 Aug 1920 | | Standard v Spartan | Franklin Field, Boston | Results |
| 28 Aug 1920 | | Brockton v West India Club A | Cross Street, Brockton | Results |
| 28 Aug 1920 | | Spartan v Needham | Franklin Field, Boston | Results |
| 28 Aug 1920 | | United Shoe Machinery, Beverly v Everett | McKay Street Athletic Park, Beverly | Results |
| 28 Aug 1920 | | West India Club B v Standard | Franklin Field, Boston | Results |
| 28 Aug 1920 | | Athletics v West Indian Wanderers | Franklin Field, Boston | Results |
| 28 Aug 1920 | | Caribbean v St George's Club of Boston | Franklin Field, Boston | Results |
| 10 Jul 1920 | | Everett v United Shoe Machinery, Beverly | Corbett Park, Everett | Results |
| 10 Jul 1920 | | Needham v Spartan | YMCA Ground, Needham | Results |
| 10 Jul 1920 | | St George's Club of Boston v Caribbean | St George's Cricket Club Ground, Boston | Results |
| 10 Jul 1920 | | West India Club A v Brockton | Franklin Field, Boston | Results |
| 10 Jul 1920 | | Standard v West India Club B | Franklin Field, Boston | Results |
| 10 Jul 1920 | | West Indian Wanderers v Athletics | Franklin Field, Boston | Results |
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