Wilbur Cross and Hillhouse High School were both constructed using identical layouts, save one elevation change between wings.

Wilbur Cross High School, built in 1926, is not only one of New Haven’s oldest educational buildings but also a facility facing significant challenges due to years of deferred maintenance.

Recent reports highlight that mold has forced the closure of critical spaces, including the library, music room, and swimming pool.

Teachers arriving on the first day of school encountered dead rodents and cockroaches while flooding in classrooms has become routine.

These dire conditions were voiced during a New Haven Board of Education meeting, where parents, teachers, and students described the school as "rotting from the inside."

Jake Halpern, president of the Wilbur Cross Parent Teacher Association, labeled the situation a crisis, urging immediate action.

However, discussions have emerged within the community about the school's capacity, as it currently exceeds its maximum enrollment by 500 students, raising concerns about potential closure or restructuring.

[citation needed] The football team plays Hillhouse High School every year on Thanksgiving in the Elm City Bowl in an annual game that dates back to 1920.

[10] The current coach of both teams, chef Nathaniel Bradshaw, won National ProStart Educator of the year in 2016.