| 2025-09-19 21:00:56September 19, 2025 |   Toronto Operario vs Annex 97 Old Boys | 3 - 1 | Over 35 Division | 2025 | Earlscourt |
| 2025-09-08 21:00:01September 8, 2025 |  Annex 97 Old Boys vs Salty Dawgs | 2 - 0 | Over 35 Division | 2025 | Thompson Park |
| 2025-09-04 20:00:14September 4, 2025 |  Annex 97 Old Boys vs Zeta FC | 6 - 1 | Over 35 Division | 2025 | Regent Park Athletic Grounds |
| 2025-08-26 20:30:55August 26, 2025 |  Etobicoke Blizzard Legends vs Annex 97 Old Boys | 1 - 11 | Over 35 Division | 2025 | Paul Coffey Park |
| 2025-08-22 21:00:16August 22, 2025 |  Annex 97 Old Boys vs GS United Pink Flamingos | 2 - 0 | Over 35 Division | 2025 | Earlscourt |
| 2025-08-17 14:00:37August 17, 2025 | Annex 97 Old Boys vs GS United Pink Flamingos | 0 - 2 | Divisional Cup | 2025 | Cherry Beach E |
| 2025-08-12 19:00:51August 12, 2025 |  Zbirdlagh vs Annex 97 Old Boys | 1 - 5 | Over 35 Division | 2025 | G.Ross Lord # 4 |
| 2025-08-07 20:00:17August 7, 2025 |  Annex 97 Old Boys vs A7M Utd | 5 - 0 | Over 35 Division | 2025 | Regent Park Athletic Grounds |
| 2025-07-28 19:00:38July 28, 2025 | KUGO vs Annex 97 Old Boys | 1 - 2 | Over 35 Division | 2025 | E.Flats NW #3 |
| 2025-07-21 21:00:19July 21, 2025 |  Annex 97 Old Boys vs Twente West Originals | 1 - 2 | Over 35 Division | 2025 | Thompson Park |
| 2025-07-14 19:00:39July 14, 2025 | Annex 97 Old Boys vs Toronto Operario | 1 - 3 | Over 35 Division | 2025 | E.Flats NW #2 |
| 2025-07-12 15:00:07July 12, 2025 |  Toronto Rovers FC vs Annex 97 Old Boys | 3 - 0 | TSSL Cup round 1 | 2025 | Cherry Beach W |
| 2025-07-08 20:30:00July 8, 2025 | Salty Dawgs vs Annex 97 Old Boys | 0 - 1 | Over 35 Division | 2025 | Paul Coffey Park |
| 2025-07-03 21:00:07July 3, 2025 | Zeta FC vs Annex 97 Old Boys | 0 - 2 | Over 35 Division | 2025 | E.Flats SE# 12 |
| 2025-06-23 21:00:47June 23, 2025 | Annex 97 Old Boys vs Etobicoke Blizzard Legends | 4 - 1 | Over 35 Division | 2025 | Thompson Park |
| 2025-06-17 21:00:39June 17, 2025 | GS United Pink Flamingos vs Annex 97 Old Boys | 2 - 1 | Over 35 Division | 2025 | G.Ross Lord # 4 |
| 2025-06-09 21:00:24June 9, 2025 | Annex 97 Old Boys vs Zbirdlagh | 3 - 3 | Over 35 Division | 2025 | Thompson Park |
| 2025-06-02 21:00:07June 2, 2025 | A7M Utd vs Annex 97 Old Boys | 0 - 3 | Over 35 Division | 2025 | Thompson Park |
| 2025-05-26 19:00:10May 26, 2025 | Annex 97 Old Boys vs KUGO | 4 - 3 | Over 35 Division | 2025 | E.Flats NW #2 |
| 2025-05-23 21:00:35May 23, 2025 | Twente West Originals vs Annex 97 Old Boys | 1 - 3 | Over 35 Division | 2025 | Weston Lions |
| 2024-10-16 20:00:53October 16, 2024 | Annex 97 Old Boys vs Toronto Operario | 3 - 0 | | | |
| 2024-10-08 19:00:24October 8, 2024 | Annex 97 Old Boys vs Etobicoke Blizzard Legends | 1 - 2 | | | |
| 2024-10-01 21:00:20October 1, 2024 | Annex 97 Old Boys vs Zeta FC | 0 - 3 | | | |
| 2024-09-22 12:15:59September 22, 2024 |  Annex 97 Old Boys vs The Herbal Cowboys | 0 - 3 | | | |
| 2024-09-16 19:00:22September 16, 2024 | Annex 97 Old Boys vs KUGO | 1 - 1 | | | |
| 2024-09-12 21:00:05September 12, 2024 | KUGO vs Annex 97 Old Boys | 1 - 0 | | | |
| 2024-09-09 21:00:57September 9, 2024 | Annex 97 Old Boys vs Zbirdlagh | 3 - 0 | | | |
| 2024-09-05 20:00:25September 5, 2024 | Annex 97 Old Boys vs Zeta FC | 2 - 3 | | | |
| 2024-09-03 20:00:16September 3, 2024 | A7M Utd vs Annex 97 Old Boys | 8 - 0 | | | |
| 2024-08-29 20:00:01August 29, 2024 | Annex 97 Old Boys vs Zbirdlagh | 2 - 1 | | | |
| 2024-08-26 20:00:51August 26, 2024 | Twente West Originals vs Annex 97 Old Boys | 1 - 0 | | | |
| 2024-08-12 19:00:41August 12, 2024 | Salty Dawgs vs Annex 97 Old Boys | 2 - 3 | | | |
| 2024-08-08 20:00:14August 8, 2024 | Annex 97 Old Boys vs A7M Utd | 0 - 4 | | | |
| 2024-08-01 19:00:56August 1, 2024 | Etobicoke Blizzard Legends vs Annex 97 Old Boys | 6 - 0 | | | |
| 2024-07-28 14:00:40July 28, 2024 | Annex 97 Old Boys vs Globe and Mail FC | 0 - 1 | | | |
| 2024-07-22 19:00:08July 22, 2024 | Annex 97 Old Boys vs Toronto Operario | 1 - 2 | | | |
| 2024-07-13 11:00:17July 13, 2024 |  Annex 97 Old Boys vs FC Torinos | 1 - 0 | | | |
| 2024-07-08 19:00:12July 8, 2024 | Zbirdlagh vs Annex 97 Old Boys | 5 - 0 | | | |
| 2024-07-02 21:00:41July 2, 2024 | Zeta FC vs Annex 97 Old Boys | 2 - 2 | | | |
| 2024-06-17 19:00:35June 17, 2024 | Annex 97 Old Boys vs Twente West Originals | 0 - 2 | | | |
| 2024-06-10 21:00:41June 10, 2024 | Annex 97 Old Boys vs Salty Dawgs | 2 - 1 | | | |
| 2024-06-03 21:00:42June 3, 2024 | A7M Utd vs Annex 97 Old Boys | 3 - 3 | | | |
| 2024-05-23 20:00:29May 23, 2024 | Toronto Operario vs Annex 97 Old Boys | 0 - 3 | | | |
| 2023-09-12 21:00:20September 12, 2023 | Annex 97 Old Boys vs Salty Dawgs | 2 - 2 | | | |
| 2023-09-07 20:00:51September 7, 2023 | Annex 97 Old Boys vs Snack Menu | 0 - 3 | | | |
| 2023-08-29 19:00:36August 29, 2023 | Annex 97 Old Boys vs Etobicoke Blizzard Legends | 1 - 7 | | | |
| 2023-08-21 18:45:02August 21, 2023 | Annex 97 Old Boys vs Kickers United | 0 - 2 | | | |
| 2023-08-14 19:00:35August 14, 2023 | Twente West Originals vs Annex 97 Old Boys | 1 - 3 | | | |
| 2023-08-12 11:00:21August 12, 2023 | Annex 97 Old Boys vs Toronto Operario | 1 - 0 | | | |
| 2023-08-10 20:00:46August 10, 2023 | Annex 97 Old Boys vs Toronto Operario | 3 - 2 | | | |
| 2023-07-31 21:00:56July 31, 2023 | Twente West Originals vs Annex 97 Old Boys | 0 - 4 | | | |
| 2023-07-24 19:00:31July 24, 2023 | Annex 97 Old Boys vs Etobicoke Blizzard Legends | 0 - 10 | | | |
| 2023-07-17 19:00:40July 17, 2023 | Kickers United vs Annex 97 Old Boys | 3 - 0 | | | |
| 2023-07-15 15:00:26July 15, 2023 |  Toronto Irish Rovers vs Annex 97 Old Boys | 0 - 3 | | | |
| 2023-07-10 19:00:29July 10, 2023 | Annex 97 Old Boys vs Salty Dawgs | 3 - 2 | | | |
| 2023-07-07 19:00:23July 7, 2023 | Annex 97 Old Boys vs Toronto Operario | 2 - 3 | | | |
| 2023-06-26 19:00:11June 26, 2023 | Zeta FC vs Annex 97 Old Boys | 2 - 2 | | | |
| 2023-06-19 19:00:10June 19, 2023 | Zbirdlagh vs Annex 97 Old Boys | 4 - 2 | | | |
| 2023-06-05 19:00:35June 5, 2023 | Snack Menu vs Annex 97 Old Boys | 1 - 1 | | | |
| 2023-05-29 21:00:28May 29, 2023 | Area7-Manic FC vs Annex 97 Old Boys | 1 - 1 | | | |
| 2023-05-25 21:00:57May 25, 2023 |  Ballers vs Annex 97 Old Boys | 1 - 4 | | | |
| 2022-09-19 21:00:24September 19, 2022 | Area7-Manic FC vs Annex 97 Old Boys | 3 - 0 | | | |
| 2022-09-12 21:00:08September 12, 2022 | Kickers United vs Annex 97 Old Boys | 0 - 1 | | | |
| 2022-09-06 19:00:44September 6, 2022 | Zbirdlagh vs Annex 97 Old Boys | 5 - 0 | | | |
| 2022-08-29 19:00:46August 29, 2022 | Twente West Originals vs Annex 97 Old Boys | 1 - 2 | | | |
| 2022-08-24 19:00:55August 24, 2022 | Annex 97 Old Boys vs Ballers | 1 - 1 | | | |
| 2022-08-15 19:00:03August 15, 2022 | Annex 97 Old Boys vs Snack Menu | 3 - 1 | | | |
| 2022-08-08 19:00:06August 8, 2022 | Annex 97 Old Boys vs Salty Dawgs | 2 - 3 | | | |
| 2022-08-04 19:00:20August 4, 2022 | Annex 97 Old Boys vs Etobicoke Blizzard Legends | 2 - 4 | | | |
| 2022-07-25 19:00:28July 25, 2022 | Toronto Operario vs Annex 97 Old Boys | 0 - 4 | | | |
| 2022-07-18 21:00:12July 18, 2022 | Annex 97 Old Boys vs Area7-Manic FC | 1 - 3 | | | |
| 2022-07-11 19:00:15July 11, 2022 | Annex 97 Old Boys vs Kickers United | 2 - 2 | | | |
| 2022-07-09 13:00:46July 9, 2022 | Roots Utd vs Annex 97 Old Boys | 0 - 3 | | | |
| 2022-07-07 19:00:20July 7, 2022 | Annex 97 Old Boys vs Zbirdlagh | 2 - 1 | | | |
| 2022-06-27 19:00:12June 27, 2022 | Annex 97 Old Boys vs Twente West Originals | 1 - 0 | | | |
| 2022-06-20 19:00:16June 20, 2022 | Ballers vs Annex 97 Old Boys | 1 - 0 | | | |
| 2022-06-13 19:00:13June 13, 2022 | Snack Menu vs Annex 97 Old Boys | 3 - 0 | | | |
| 2022-06-06 19:00:35June 6, 2022 | Salty Dawgs vs Annex 97 Old Boys | 2 - 1 | | | |
| 2022-05-30 19:00:38May 30, 2022 | Etobicoke Blizzard Legends vs Annex 97 Old Boys | 1 - 6 | | | |
| 2022-05-25 19:00:24May 25, 2022 | Annex 97 Old Boys vs Toronto Operario | 1 - 6 | | | |
