SHS News
The Staples Wreckers boys' soccer team won the state championship on November 16, 2025, defeating Greenwich 3-0 in the Class LL final. This victory marks the program's 13th state title and its first since 2009. Read more at Staplessoccer.com. Photo credit: David G. Whitman for the Ruden Report, posted on Staples Soccer.
On October 22, forty-four Staples High School students attended Sports Business Day at MetLife Stadium, an immersive learning event hosted by the New York Jets. The program brought together over 1,000 students from across the region to explore the professional opportunities that exist off the field within the sports industry.
After last week’s milestone, when sophomores became the first student-led belay group to complete the “Leap of Faith” on the Staples outdoor challenge course, the Superintendent joined them to experience the thrill himself.
Staples High School is proud to celebrate several remarkable achievements by members of its school community, highlighting the talent, dedication, and excellence that define Westport Public Schools.
Sophomore students at Staples High School recently reached new heights—literally—during a physical education class that became the first student-led belay group to complete the “Leap of Faith” on the school’s outdoor challenge course.
The New York Giants and Gatorade have selected Mr. Matty Jacowleff of Staples High School (Westport, CT) as the Lou Rettino High School Coach of the Week for Week 6 of the 2025 season. The Wreckers improved to 4-0 on the season in Jacowleff’s inaugural campaign as head coach and upset the Darien Blue Wave on the road by a score of 31-6. It was the first victory for Staples over Darien in 13 years.
