The secondary school is known for their competitive sports, extremely strong academics, arts, their bulldog mascot and extensive list of extracurriculars.

It was named after the British Prime Minister, who led the United Kingdom through the Second World War.

Sir Winston Churchill's Extended French program has been in existence for over 30 years.

[1] Sir Winston Churchill offers several extracurricular sports activities to its students, including football, swimming, cross country running, track and field, volleyball, basketball, soccer, lacrosse, hockey, badminton, rowing, and others.

The Sir Winston Churchill Sr. Football team won the Niagara Regional High School Championship in the 2024 season.