The early 1930s saw a string of five County Class 'B' Championships, climaxed by Roxbury's only undefeated season in 1934, when the team won the Morris County title and finished with an 8-0-2 record. The 1941 team, known as the Galloping Gaels, registered six shutouts. In addition to winning the Morris County Championship, the 1942 team posted the Gaels' 100th victory. The 1959 team won the school's third state championship, being declared North II, Group II champions after finishing the season with a 6-2-1 mark. Roxbury's 200th win came in 1964 and the 300th win came in 1979, a 30–10 win over Dover High School. Roxbury's 400th win was in 1998 over Columbia High School, 40–0. The 500th win was in 2014 over Morristown High School.