- Cup Round: Preliminary
- Cup Round: Preliminary 2
- Cup Round:Round of 32
- Cup Round: Round of 16
- Quarter-Finals
- Semi-Finals
- Finals
 
3 - 0TSSL Cup round 1
2025
E.Flats NW #1
FC Torinos vs Etobicoke Blizzard Legends |
 
3 - 1TSSL Cup round 1
2025
E.Flats NW #1
New Junction FC vs GS United Pink Flamingos |
 
0 - 3TSSL Cup round 1
2025
Cherry Beach W
Twente West Originals vs Bizzos FC |
 
3 - 0TSSL Cup round 1
2025
Cherry Beach W
Toronto Rovers FC vs Annex 97 Old Boys |
 
3 - 0TSSL Cup Round 32
2025
G.Ross Lord # 4
Tropa de Elite FC vs Zeta FC |
3 - 0TSSL Cup Round 32
2025
G.Ross Lord # 4
System 3 vs Inter Toronto CF |
0 - 3TSSL Cup Round 32
2025
Cherry Beach E
Mississauga Stingers vs SC Dacia |
 
3 - 0TSSL Cup Round 32
2025
Cherry Beach E
Kensington Rovers vs Toronto Slovenia |
1 - 2TSSL Cup Round 32
2025
E.Flats NW #3
Islington United vs A7M Utd |
 
0 - 3TSSL Cup Round 32
2025
E.Flats NW #1
SA Ukraina vs LOSTRACCOS FC |
 
4 - 1TSSL Cup Round 32
2025
Cherry Beach E
Kensington Rovers II vs Toronto Irish Rovers |
3 - 0TSSL Cup Round 32
2025
Cherry Beach E
Luton Shamrocks II vs Caribbean Stars |
 
0 - 3TSSL Cup Round 32
2025
Cherry Beach W
Annex FC III vs America United FC |
4 - 1TSSL Cup Round 32
2025
E.Flats NW #1
Hungaria FTC vs Bizzos FC |
 
7 - 1TSSL Cup Round 32
2025
E.Flats NW #1
Toronto Operario vs Sauce FC |
2 - 3TSSL Cup Round 32
2025
Cherry Beach E
New Junction FC vs Real Nomads FC |
0 - 3TSSL Cup Round 32
2025
E.Flats NW #4
Globe and Mail FC vs The Herbal Cowboys |
0 - 3TSSL Cup Round 32
2025
L'amoreaux North # 5
Toronto Rovers FC vs Annex II |
5 - 3TSSL Cup Round 32
2025
E.Flats NW #4
Luton Shamrocks vs Scar Bros |
3 - 0TSSL Cup Round 16
2025
G.Ross Lord # 4
Kensington Rovers vs System 3 |
0 - 3TSSL Cup Round 16
2025
E.Flats SE# 11
A7M Utd vs Annex II |
3 - 0TSSL Cup Round 16
2025
Cherry Beach E
Real Nomads FC vs SC Dacia |
2 - 1TSSL Cup Round 16
2025
E.Flats NW #4
Toronto Operario vs Luton Shamrocks II |
4 - 5TSSL Cup Round 16
2025
E.Flats NW #4
The Herbal Cowboys vs Tropa de Elite FC |
3 - 1TSSL Cup Round 16
2025
Cherry Beach W
Luton Shamrocks vs Hungaria FTC |
3 - 0TSSL Cup Round 16
2025
E.Flats NW #4
FC Torinos vs LOSTRACCOS FC |
1 - 2Tssl Cup Quarter Finals
2025
Cherry Beach E
Kensington Rovers vs Luton Shamrocks |
2 - 4Tssl Cup Quarter Finals
2025
Weston Lions
Annex II vs FC Torinos |
3 - 1Tssl Cup Quarter Finals
2025
Weston Lions
Tropa de Elite FC vs Real Nomads FC |
3 - 4Tssl Cup Quarter Finals
2025
Weston Lions
Kensington Rovers II vs Toronto Operario |
1 - 3TSSL Cup Semi Finals
2025
Weston Lions
FC Torinos vs Toronto Operario |
0 - 3TSSL Cup Semi Finals
2025
L'amoreaux North # 5
Tropa de Elite FC vs Luton Shamrocks |
12:00 pmTSSL CUP Final
2025
Weston Lions
Luton Shamrocks vs Toronto Operario |