| 2016-04-10 14:00:35April 10, 2016 | Boston Olympiakos vs Sharp | 10 - 0 | N/A | Recap |
| 2016-04-24 14:00:29April 24, 2016 | Boston Olympiakos vs Green Briar | 4 - 2 | N/A | Recap |
| 2016-05-01 18:00:20May 1, 2016 | Boston Olympiakos vs Southie FC | 18:00:206:00 PM | N/A | Recap |
| 2016-05-08 12:00:02May 8, 2016 | Boston Olympiakos vs Celtic | 7 - 0 | N/A | Recap |
| 2016-05-15 13:00:29May 15, 2016 | Boston Olympiakos vs Homenetmen | 5 - 0 | N/A | Recap |
| 2016-05-22 18:00:07May 22, 2016 | Boston Olympiakos vs Essex County | 4 - 1 | N/A | Recap |
| 2016-06-05 15:00:29June 5, 2016 | Boston Olympiakos vs Ethiopians | 15:00:293:00 PM | N/A | Recap |
| 2016-06-12 14:00:13June 12, 2016 | Boston Olympiakos vs Skenderbeu | 3 - 1 | N/A | Recap |
| 2016-06-19 15:00:33June 19, 2016 | Boston Olympiakos vs Ethiopians | 4 - 2 | N/A | Recap |
| 2016-06-23 20:00:48June 23, 2016 | Boston Olympiakos vs Ethiopians | 6 - 1 | N/A | Recap |
| 2016-06-26 17:30:30June 26, 2016 | Boston Olympiakos vs Albania | 17:30:305:30 PM | N/A | Recap |
| 2016-07-06 20:00:39July 6, 2016 | Boston Olympiakos vs Southie FC | 4 - 4 | N/A | Recap |
| 2016-07-17 10:00:36July 17, 2016 | Safira FC vs OXford | 10:00:3610:00 AM | N/A | Recap |
| 2016-07-17 10:30:48July 17, 2016 | Valeo FC vs Strela Negra | 10:30:4810:30 AM | N/A | Recap |
| 2016-07-24 10:00:12July 24, 2016 | Dorchester United vs Albania United | 10:00:1210:00 AM | N/A | Recap |
| 2016-07-24 10:30:47July 24, 2016 | Boston Olympiakos vs Brockton United | 10:30:4710:30 AM | N/A | Recap |
| 2016-07-24 12:30:26July 24, 2016 | Mosteiro FM vs GPS | 12:30:2612:30 PM | N/A | Recap |
| 2016-08-14 19:00:58August 14, 2016 | Boston Olympiakos vs Lowell United | 4 - 1 | N/A | Recap |
| 2016-08-21 15:00:59August 21, 2016 | Boston Olympiakos vs Mill City | 1 - 1 | N/A | Recap |
| 2016-08-28 13:00:42August 28, 2016 | Boston Olympiakos vs Albania | 4 - 3 | N/A | Recap |
| 2016-09-11 00:00:34September 11, 2016 | Boston Olympiakos vs Southie FC | 00:00:3412:00 AM | N/A | Recap |
| 2016-09-18 15:00:22September 18, 2016 | Boston Olympiakos vs Green Briar | 6 - 1 | N/A | Recap |
| 2016-09-25 15:00:57September 25, 2016 | Boston Olympiakos vs Lowell United | 7 - 1 | N/A | Recap |
| 2016-10-02 19:30:47October 2, 2016 | Boston Olympiakos vs Mill City | 2 - 2 | N/A | Recap |
| 2016-10-16 15:00:26October 16, 2016 | Boston Olympiakos vs Albania | 6 - 1 | N/A | Recap |
| 2016-10-23 15:00:24October 23, 2016 | Boston Olympiakos vs Southie FC | 3 - 0 | N/A | Recap |
| 2016-10-26 20:00:57October 26, 2016 | Boston Olympiakos vs Southie FC | 2 - 0 | N/A | Recap |
| 2016-10-30 12:00:52October 30, 2016 | Boston Olympiakos vs Green Briar | 12:00:5212:00 PM | N/A | Recap |
| 2016-11-13 13:00:23November 13, 2016 | Boston Olympiakos vs Safira FC | 2 - 1 | N/A | Recap |
| 2016-11-20 13:00:17November 20, 2016 | Boston Olympiakos vs Safira FC | 2 - 1 | N/A | Recap |
| 2016-11-27 13:00:35November 27, 2016 | Boston Olympiakos vs Southie FC | 13:00:351:00 PM | N/A | Recap |
| 2016-12-04 13:00:04December 4, 2016 | Boston Olympiakos vs Albania | 13:00:041:00 PM | N/A | Recap |
| 2017-03-05 14:00:34March 5, 2017 | Boston Olympiakos vs Tarrafal | 14:00:342:00 PM | N/A | Recap |
| 2017-03-12 14:00:15March 12, 2017 | Boston Olympiakos vs Atletico Junior | 14:00:152:00 PM | N/A | Recap |
| 2017-03-19 14:00:19March 19, 2017 | Boston Olympiakos vs TBD | 14:00:192:00 PM | N/A | Recap |
| 2017-03-26 12:00:31March 26, 2017 | Boston Olympiakos vs Safira FC | 12:00:3112:00 PM | N/A | Recap |
| 2017-04-02 16:00:53April 2, 2017 | Boston Olympiakos vs Athletico B | 5 - 1 | N/A | Recap |
| 2017-04-09 12:00:57April 9, 2017 | Boston Olympiakos vs Mill City | 12:00:5712:00 PM | N/A | Recap |
| 2017-04-23 12:00:33April 23, 2017 | Boston Olympiakos vs Ethiopians | 4 - 2 | N/A | Recap |
| 2017-04-30 12:00:06April 30, 2017 | Boston Olympiakos vs Mill City | 12:00:0612:00 PM | N/A | Recap |
| 2017-05-07 18:00:47May 7, 2017 | Boston Olympiakos vs Lowell United | 0 - 1 | N/A | Recap |
| 2017-05-14 12:00:34May 14, 2017 | Boston Olympiakos vs Athletico Jr | 2 - 2 | N/A | Recap |
| 2017-05-21 12:00:13May 21, 2017 | Boston Olympiakos vs Athletico B | 10 - 1 | N/A | Recap |
| 2017-06-04 12:00:48June 4, 2017 | Boston Olympiakos vs Ethiopians | 1 - 1 | N/A | Recap |
| 2017-06-11 12:00:55June 11, 2017 | Boston Olympiakos vs Golden Boys | 4 - 0 | N/A | Recap |
| 2017-06-18 12:00:04June 18, 2017 | Boston Olympiakos vs Lowell United | 4 - 0 | N/A | Recap |
| 2017-06-21 12:00:47June 21, 2017 | Boston Olympiakos vs Golden Boys | 8 - 1 | N/A | Recap |
| 2017-06-25 12:00:19June 25, 2017 | Boston Olympiakos vs Athletico Jr | 0 - 5 | N/A | Recap |
| 2017-07-02 16:00:39July 2, 2017 | Boston Olympiakos vs Golden Boys | 3 - 0 | N/A | Recap |
| 2017-07-09 16:00:24July 9, 2017 | Boston Olympiakos vs Golden Boys | 16:00:244:00 PM | N/A | Recap |
| 2017-08-13 15:00:17August 13, 2017 | Boston Olympiakos vs Ethiopians | 4 - 2 | N/A | Recap |
| 2017-08-20 15:00:52August 20, 2017 | Boston Olympiakos vs Ethiopians | 3 - 2 | N/A | Recap |
| 2017-09-17 15:00:26September 17, 2017 | Boston Olympiakos vs Lowell United | 3 - 0 | N/A | Recap |
| 2017-09-24 12:00:52September 24, 2017 | Ethiopians vs Boston Olympiakos | 0 - 0 | N/A | Recap |
| 2017-10-01 13:00:20October 1, 2017 | Boston Olympiakos vs Athletico Jr | 5 - 3 | N/A | Recap |
| 2017-10-08 13:00:10October 8, 2017 | Boston Olympiakos vs Ethiopians | 5 - 3 | N/A | Recap |
| 2017-10-15 14:00:43October 15, 2017 | Boston Olympiakos vs Juve Pro-Soccer | 14:00:432:00 PM | N/A | Recap |
| 2017-10-22 13:00:52October 22, 2017 | Boston Olympiakos vs Lowell United | 3 - 2 | N/A | Recap |
| 2017-10-29 13:00:24October 29, 2017 | Boston Olympiakos vs Lowell United | 13:00:241:00 PM | N/A | Recap |
| 2017-11-05 13:00:14November 5, 2017 | Boston Olympiakos vs BCSXI | 4 - 0 | N/A | Recap |
| 2017-11-11 12:00:48November 11, 2017 | Boston Olympiakos vs Warehouse Gunners | 12:00:4812:00 PM | N/A | Recap |
| 2018-04-22 16:00:06April 22, 2018 | Boston Olympiakos vs Athletico B | 3 - 3 | N/A | Recap |
| 2018-04-29 16:00:05April 29, 2018 | Boston Olympiakos vs Ethiopians | 2 - 4 | N/A | Recap |
| 2018-05-06 16:00:46May 6, 2018 | Boston Olympiakos vs Athletico Jr | 6 - 0 | N/A | Recap |
| 2018-05-13 16:00:26May 13, 2018 | Boston Olympiakos vs Athletico B | 16:00:264:00 PM | N/A | Recap |
| 2018-05-20 16:00:49May 20, 2018 | Boston Olympiakos vs Athletico Jr | 5 - 0 | N/A | Recap |
| 2018-06-03 16:00:12June 3, 2018 | Boston Olympiakos vs Athletico B | 2 - 1 | N/A | Recap |
| 2018-06-10 16:00:52June 10, 2018 | Boston Olympiakos vs Athletico B | 2 - 1 | N/A | Recap |
| 2018-06-17 16:00:15June 17, 2018 | Boston Olympiakos vs Ethiopians | 3 - 3 | N/A | Recap |
| 2018-08-19 16:00:50August 19, 2018 | Boston Olympiakos vs Athletico B | 2 - 2 | N/A | Recap |
| 2018-08-26 13:00:45August 26, 2018 | Boston Olympiakos vs Ethiopians | 2 - 5 | N/A | Recap |
| 2018-09-09 13:00:08September 9, 2018 | Boston Olympiakos vs Athletico Jr | 3 - 0 | N/A | Recap |
| 2018-09-16 16:00:43September 16, 2018 | Boston Olympiakos vs Athletico B (CUP) | 3 - 0 | N/A | Recap |
| 2018-09-23 16:00:05September 23, 2018 | Boston Olympiakos vs Athletico Jr | 7 - 2 | N/A | Recap |
| 2018-09-30 16:00:08September 30, 2018 | Boston Olympiakos vs Athletico B | 3 - 0 | N/A | Recap |
| 2018-10-07 16:00:12October 7, 2018 | Boston Olympiakos vs Ethiopians | 5 - 2 | N/A | Recap |
| 2018-10-14 14:00:43October 14, 2018 | Athletico Jr vs Ethiopians | 4 - 0 | N/A | Recap |
| 2018-10-21 13:30:12October 21, 2018 | Boston Olympiakos vs Ethiopians | 7 - 2 | N/A | Recap |
| 2019-04-14 13:00:03April 14, 2019 | Boston Olympiakos vs Boston Siege FC II | 1 - 3 | N/A | Recap |
| 2019-06-30 13:00:08June 30, 2019 | Boston Olympiakos vs Athletico B | 2 - 0 | N/A | Recap |
| 2019-08-18 13:00:11August 18, 2019 | Boston Olympiakos vs Boston Siege FC II | 5 - 2 | N/A | Recap |
| 2019-08-25 13:00:39August 25, 2019 | Boston Olympiakos vs Athletico Jr | 13:00:391:00 PM | N/A | Recap |
| 2019-09-08 13:00:35September 8, 2019 | Boston Olympiakos vs United Hands | 13:00:35TBD | N/A | Recap |
| 2019-09-15 13:00:15September 15, 2019 | Boston Olympiakos vs Athletico B | 13:00:15TBD | N/A | Recap |
| 2019-09-29 13:00:49September 29, 2019 | Boston Olympiakos vs Boston Ethiopians | 13:00:49TBD | N/A | Recap |
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