The team is a member of the Patriot League, an NCAA Division I conference that participates in the Football Championship Subdivision (FCS).

The first intercollegiate game played on campus was a 6–0 defeat of Massachusetts Agricultural College on September 26, 1903, on the site of what is now Hanover Insurance Park at Fitton Field.

Since 1910, the Holy Cross Crusader "Goodtime" Marching Band has performed halftime shows at home football games.

The largest crowd ever to pack Fitton Field was the 27,000 who showed up to see Holy Cross's All-American back Bill Osmanski in his last home game in 1938.

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.

The Eagles had booked their victory party that night at the popular Cocoanut Grove nightclub in Boston, but canceled after the loss.

After an over three-decade hiatus, the series resumed in 2018 as Holy Cross traveled to Chestnut Hill to take on Boston College.

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.

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.

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.

In poor weather conditions, the Crusaders took out New Hampshire 35-19 in Worcester to advance to play #1 overall seed South Dakota State, eventually losing 42-21.