| Senior Boys Football (Tier) |
| Friday, September 22, 2023 |
|
Visitor
|
Score |
Score |
Home |
Sir Winston Churchill SS |
0
| 52 |
Westmount SS |
|
|
Location: Westmount SS 
|
Notes:
Regular Season. |
|
| Thursday, September 28, 2023 |
|
Visitor
|
Score |
Score |
Home |
Saltfleet DHS |
37
| 0 |
Sir Winston Churchill SS |
|
|
| Location: Sir Winston Churchill SS
|
Notes:
Regular Season. |
|
| Thursday, October 5, 2023 |
|
Visitor
|
Score |
Score |
Home |
Ancaster HS |
28
| 7 |
Sir Winston Churchill SS |
|
|
| Location: Sir Winston Churchill SS
|
Notes:
Regular Season. |
|
| Thursday, October 12, 2023 |
|
Visitor
|
Score |
Score |
Home |
|
Sir Winston Churchill SS |
8
| 36 |
Westdale SS |
|
|
| Location: Westdale SS
|
Notes:
Regular Season. |
|
| Thursday, October 19, 2023 |
|
Visitor
|
Score |
Score |
Home |
Dundas Valley SS |
23
| 20 |
Sir Winston Churchill SS |
|
|
| Location: Sir Winston Churchill SS
|
Notes:
Regular Season. |
|
| Thursday, November 2, 2023 |
|
Visitor
|
Score |
Score |
Home |
Bernie Custis SS |
8
| 47 |
Sir Winston Churchill SS |
|
|
| Location: Sir Winston Churchill SS
|
Notes:
Semi Final. |
|
| Wednesday, November 8, 2023 |
|
Visitor
|
Score |
Score |
Home |
Sherwood SS |
0
| 37 |
Sir Winston Churchill SS |
|
|
| Location: Waterdown DHS
|
Notes:
Playoff Final. Chayka |
|
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