The Bombers defeated Stamford Collegiate Secondary School in Niagara Falls, Ontario for the first-ever international title on October 5, 1940,[5] and were ranked in the top 10 in the nation by The American Boy magazine.

Due to increasing enrollment from the construction of the Ravenna Arsenal a decade earlier,[4] Windham was close to "AA" classification.

However, in contests against Garrettsville and Ravenna Township, football coach Leo Kot played two freshmen to prevent running up the score.

These contests led directly to Windham's classification as "AA" upon appeal from Mogadore High School, and the subsequent formation of the Tomahawk Conference.

[8] In its first three years of competition, Windham won several league championships in volleyball and girls basketball.