| Total | 20 | 6 | (30%) | 2 | (10%) | 12 | (60%) |
| Casa | 9 | 6 | (67%) | 1 | (11%) | 2 | (22%) |
| Fuera | 11 | 0 | (0%) | 1 | (9%) | 10 | (91%) |
D | 2019-10-19 | Scarborough SC |  | 4-2 |  | Kingsman SC | SF | ||
E | 2019-10-12 | FC Vorkuta |  | 2-2(2-4 pen.) | | Kingsman SC | CF | ||
D | 2019-10-05 | Hamilton City |  | 3-1 | | Kingsman SC | J18 | ||
D | 2019-10-03 | Serbian White Eagles |  | 3-1 | | Kingsman SC | J18 | ||
D | 2019-09-28 | CSC Mississauga |  | 7-2 | | Kingsman SC | J17 | ||
D | 2019-09-15 | Ukraine United |  | 5-1 | | Kingsman SC | J15 | ||
V | 2019-09-07 | Kingsman SC | | 3-2 | | Hamilton City | J14 | ||
D | 2019-08-25 | Brantford Galaxy |  | 3-1 | | Kingsman SC | J13 | ||
D | 2019-08-18 | Scarborough SC | | 2-1 | | Kingsman SC | J12 | ||
E | 2019-08-10 | Kingsman SC | | 3-3 | | Scarborough SC | J11 | ||
V | 2019-08-03 | Kingsman SC | | 4-2 | | Serbian White Eagles | J10 | ||
D | 2019-07-27 | Kingsman SC | | 0-3 | | FC Vorkuta | J9 | ||
V | 2019-07-21 | Kingsman SC | | 2-1 |  | SC Waterloo | J8 | ||
V | 2019-07-05 | Kingsman SC | | 2-1 | | Ukraine United | J6 | ||
V | 2019-06-28 | Kingsman SC | | 4-0 | | Brantford Galaxy | J5 | ||
D | 2019-06-22 | Real Mississauga |  | 3-0 | | Kingsman SC | J5 | ||
D | 2019-06-16 | Kingsman SC | | 0-4 | | CSC Mississauga | J4 | ||
D | 2019-06-08 | SC Waterloo | | 3-1 | | Kingsman SC | J3 | ||
V | 2019-06-02 | Kingsman SC | | 2-0 | | Real Mississauga | J2 | ||
D | 2019-05-25 | FC Vorkuta | | 4-2 | | Kingsman SC | J1 |
