Boston College rivalry

In 1896, Holy Cross and Boston College played the first football game between the two schools, starting the Boston College–Holy Cross football rivalry. For much of the early to mid 20th century, BC and The Cross drew some of New England's largest sports crowds. To accommodate larger crowds, the Holy Cross game was routinely held at a large venue in Boston, with the 1916 matchup taking place at the newly constructed Fenway Park. A record 54,000 attended the 1922 game at Braves Field, home of the Boston Braves baseball team. On November 28, 1942, Holy Cross beat BC in a huge upset 55–12. The game is still the most famous between the two foes, not only for its result (which spoiled BC's undefeated season) but also its aftermath. The Eagles had booked their victory party that night at the popular Cocoanut Grove nightclub in Boston, but canceled after the loss. As a result, the BC team was absent when the club caught fire, killing nearly 500.

But fortune did not always favor the Crusaders, and the series was suspended in 1986 after BC had won 17 games over a 20-year span. After an over three-decade hiatus, the series resumed in 2018 as Holy Cross traveled to Chestnut Hill to take on Boston College. A rematch was held in 2023, which BC won 31–28.

1946 Orange Bowl

In 1945, Holy Cross brought its best team in school history to the Orange Bowl only to feel the heartbreak it had given BC three years earlier. On January 1, 1946, Holy Cross lost a heartbreaker to the University of Miami in its only bowl appearance. With the score tied 6–6 and only seconds remaining in regulation, Holy Cross was intercepted by Miami's Al Hudson, who ran the ball 89 yards for a touchdown. The final score was 13–6.

A glorious decade

In 1969, Holy Cross had to cancel the final eight games of the season when a contaminated faucet on a practice field led to an outbreak of hepatitis. Through the 1970s Holy Cross continued to play major East Coast football powers, but the Crusaders struggled to compete with the bigger schools.

In 1981, the NCAA dropped Holy Cross from the upper tier of football competition to Division I-AA. Holy Cross enjoyed a football renaissance over the next decade under coaches Rick E. Carter (35–19–2) and especially Mark Duffner (60–5–1). In 1983, the team was No. 3 in the nation in I-AA under Carter. Under Duffner, Holy Cross became the nation's most successful I-AA program. There were 11–0 seasons in both 1987 and 1991. Holy Cross won five Colonial League and Patriot League championships, four Lambert Cups, and four ECAC Team of the Year Awards. It also earned the No. 1 ranking in the final 1987 NCAA Division I-AA poll. In 1987 running back/defensive back Gordie Lockbaum finished third in the Heisman Trophy balloting after finishing fifth in 1986.

In the midst of these winning seasons, Holy Cross changed the direction of its football program. In 1986 it joined the Colonial League, a football-only conference that adopted the Ivy League model of need-based financial aid and grants rather than formal athletic scholarships. In 1990, the Colonial League became an all-sports conference and changed its name to the Patriot League; over time, it began allowing scholarships in non-football sports (with the recipients ineligible to play football), but continued to prohibit football scholarships through the 2012 season. In 2013, the Patriot League transitioned back to traditional scholarship football following Fordham’s decision to offer football scholarships in 2010.

2009 season

In 2009, Holy Cross had one of its best teams since the founding of the Patriot League, led by star quarterback Dominic Randolph. The Crusaders won the league title and earned an automatic berth to the FCS playoffs, where they lost in the first round to eventual national champion Villanova.

The Chesney Era

Bob Chesney took over as Holy Cross head coach in 2018. In his first season, the Crusaders won their last 4 games to finish second in the Patriot League. In 2019 the Crusaders won the league title and earned an automatic berth to the FCS playoffs, where they lost in the first round to Monmouth. In a shortened 2021 spring season, the Crusaders went undefeated and won the league title for the second year in a row. In the fall 2021 season, the Crusaders won their third Patriot League Championship in a row. The season also marked the first FCS playoff victory for Holy Cross, a 13-10 win over Sacred Heart in the first round. The Crusaders saw their season end once again at the hands of Villanova, however. The 2022 season saw the team post an undefeated 11–0 regular season record, highlighted by a win at FBS opponent Buffalo and a sweep of Harvard and Yale. Their success saw them receive the #8 seed in the FCS playoffs, which carried with it a first-round bye and a home game in the round of 16. In poor weather conditions, the Crusaders took out New Hampshire 35-19 in Worcester to advance to play #1 overall seed South Dakota State.

Chesney left the program following the 2023 season after being hired by James Madison.^[3]