- Cup Round: Preliminary
- Cup Round: Preliminary 2
- Cup Round:Round of 32
- Cup Round: Round of 16
- Quarter-Finals
- Semi-Finals
- Finals
7 - 0TSSL Cup Preliminary
2023
Centennial Park C
Hungaria FTC vs Zeta FC |
5 - 1TSSL Cup Preliminary
2023
E.Flats SE# 11
Area7-Manic FC vs Sauce FC |
3 - 0TSSL Cup Preliminary
2023
Cherry Beach W
Toronto Irish Rovers vs Annex 97 Old Boys |
5 - 1TSSL Cup Preliminary 2
2023
Earlscourt
Hungaria FTC vs Twente West Originals |
3 - 1TSSL Cup Preliminary 2
2023
Cherry Beach W
Toronto Irish Rovers vs Area7-Manic FC |
3 - 4TSSL Cup Round 32
2023
E.Flats NW #3
Annex II vs GS FC |
3 - 2TSSL Cup Round 32
2023
E.Flats NW #4
FC Torinos vs Morton |
3 - 0TSSL Cup Round 32
2023
Cherry Beach E
LOSTRACCOS FC vs Ethio Walia SC |
3 - 1TSSL Cup Round 32
2023
E.Flats NW #3
Luton Shamrocks II vs Toronto Rovers FC |
3 - 0TSSL Cup Round 32
2023
E.Flats NW #4
Caribbean Stars vs Globe and Mail FC |
2 - 5TSSL Cup Round 32
2023
E.Flats NW #4
Roots Utd vs Islington United |
3 - 0TSSL Cup Round 32
2023
Cherry Beach E
Annex FC vs Nations United |
2 - 3TSSL Cup Round 32
2023
Cherry Beach E
Real Nomads FC vs Toronto City FC |
2 - 3TSSL Cup Round 32
2023
E.Flats SE# 11
Toronto Operario vs Kensington Rovers II |
0 - 3TSSL Cup Round 32
2023
Cherry Beach W
New Junction FC vs System 3 |
0 - 5TSSL Cup Round 32
2023
Cherry Beach E
Toronto Irish vs America United FC |
3 - 0TSSL Cup Round 32
2023
E.Flats NW #4
TT Boys FC vs Etobicoke Blizzard |
7 - 3TSSL Cup Round 32
2023
Cherry Beach E
SC Dacia vs Toronto Slovenia |
1 - 2TSSL Cup Round 32
2023
E.Flats NW #4
Luton Shamrocks vs The Herbal Cowboys |
2 - 1TSSL Cup Round 32
2023
Cherry Beach W
Scar Bros vs Hungaria FTC |
1 - 2TSSL Cup Round 32
2023
Downsview Park Field 3
Kensington Rovers vs Toronto Irish Rovers |
1 - 0TSSL Cup Round 16
2023
E.Flats NW #4
Luton Shamrocks II vs FC Torinos |
3 - 0TSSL Cup Round 16
2023
Cherry Beach E
Annex FC vs LOSTRACCOS FC |
0 - 3TSSL Cup Round 16
2023
E.Flats NW #1
Islington United vs The Herbal Cowboys |
2 - 1TSSL Cup Round 16
2023
E.Flats NW #4
Scar Bros vs GS FC |
3 - 0TSSL Cup Round 16
2023
E.Flats NW #4
SC Dacia vs Toronto City FC |
4 - 5TSSL Cup Round 16
2023
E.Flats NW #4
Caribbean Stars vs TT Boys FC |
0 - 3TSSL Cup Round 16
2023
Cherry Beach W
Toronto Irish Rovers vs America United FC |
1 - 2TSSL Cup Round 16
2023
Cherry Beach W
Kensington Rovers II vs System 3 |
0 - 1Tssl Cup Quarter Finals
2023
Cherry Beach E
Annex FC vs Luton Shamrocks II |
1 - 0Tssl Cup Quarter Finals
2023
Cherry Beach E
Scar Bros vs System 3 |
3 - 0Tssl Cup Quarter Finals
2023
Cherry Beach E
America United FC vs TT Boys FC |
0 - 3Tssl Cup Quarter Finals
2023
Cherry Beach E
SC Dacia vs The Herbal Cowboys |
1 - 0TSSL Cup Semi Finals
2023
G.Ross Lord # 4
Scar Bros vs Luton Shamrocks II |
8 - 1TSSL Cup Semi Finals
2023
Cherry Beach E
America United FC vs The Herbal Cowboys |
2 - 4TSSL CUP Final
2023
Weston Lions
Scar Bros vs America United FC |