The 1928 team won the second state championship in school history, in the team's only season with Coach Robert Mohor. The first of Roxbury's early rivals was Dover High School, who they beat for the first time in 1917 by a score of 7–6. A turkey dinner was given to the team whenever they topped the Tigers. By 1929, Hackettstown High School became the annual Thanksgiving Day contest. The series ended in 1976 with a 34-7 Gael victory; Roxbury and Hackettstown have not played since. One of the most intense rivalries in the state began in 1965 against Randolph High School. 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. The '86 and '87 teams advanced to the state tournament finals, losing to Union High School on both occasions. 1987 was the senior season of Dave Moore '88, a future NFL pro-bowler, whose #88 became the team's first number to be retired.  2002 marked Head Coach Cosmo Lorusso's first year in Roxbury, when the Gaels made the sectional semi-finals and finished as IHC-Iron Tri-Champions. The 2009 team jumped to an 8–0 start, quickly winning the inaugural Northwest Jersey Athletic Conference-American Division championship. After two sound victories to start the '09 postseason, Roxbury faced East Orange Campus High School in the state sectional championship, played at Giants Stadium, winning 14-6 and clinching the fifth state title in school history, as well as setting the school record for wins in a season with 11. In 2012, the Roxbury High School Football Gaels played their 100th season of football, celebrating it with an 11–1 season and the program's sixth state championship with a 14–6 victory over Pascack Valley High School in the North I Group IV finals at Kean University.