Monmouth College's first official football game was played in 1891 against Knox College. Since that time, the Monmouth-Knox rivalry has become a big part of the history and tradition of Fighting Scot football. Monmouth was crowned "college champions of Illinois" in 1905 and repeated in 1906 when the team recorded its first perfect season at 8-0. Hall of Famer Francis "Jug" Earp, who would go on to play 11 seasons of professional football with the Green Bay Packers, dominated the Fighting Scot offensive line in the early 1920s and the Warren Taylor-Keith Molesworth passing combination of the mid-'20s was one of the finest the college has ever produced. Molesworth would later play eight NFL seasons with the Chicago Bears.

Herbert Hart was coach when the Scots joined the fledgling Midwest Collegiate Athletic Conference in 1925 and Monmouth was quick to establish its athletic reputation, again going undefeated and earning co-champion honors of the league at 7-0-2. The team's offensive attack was so dominant that year it gained the nickname "The Trick-A-Minute Machine". Monmouth claimed a share of the MCAC title three more times under Hart in the early '30s before his retirement as football coach and athletic director in 1938. Robert "Bobby" Woll, one of the best all-around athletes ever to wear a Monmouth jersey and the only person to have his number retired at the college, was the star during the 1931-33 seasons. In 1981 the new football field was dedicated and named Bobby Woll Athletic Field in honor of Woll's years of competition and coaching service at Monmouth.

Glenn "Jelly" Robinson, a former player under Hart, became head coach in 1941 and guided the Scots for 14 years, compiling a 49-56-6 career record. Robinson's best season was in 1952 when his team posted a 6-2 mark, losing only to MWC rivals Coe and St. Olaf by a mere five points. The 1952 and 1953 squads featured the rushing prowess of All-American tailback Ray Brooks. The arrival of Bill Reichow in 1966 marked the resurgence of Monmouth as a Midwest Conference football title contender. Reichow's teams won three league championships and placed second four times in his 13 years as head coach. The 1972 squad posted the best record of any Monmouth team, winning the MCAC championship with a perfect 9-0 record. Reichow's career coaching totals of 78-31-2, including a record 17-game consecutive win streak from 1971-73, and .716 winning percentage are the best among Fighting Scot coaches. Reichow's teams featured two of the best running backs to ever play at Monmouth in Charlie Corle (1967-69) and Ron Baker (1972-75), who ended his career as the team's all-time leading rusher with 3,642 yards.

Following a few lean seasons, current head coach Kelly Kane took over the reins in the fall of 1984 and turned the program back in the right direction. Kane guided Monmouth to the MCAC league championship game in 1987 and the Scots enjoyed a three-year run as South Division champions. Despite dropping all three title games to St. Norbert in close decisions, Monmouth football had regained its reputation in the conference as a tough and ready opponent. Following a heartbreaking 3-0 home loss to Coe in the infamous 1986 "Mud Bowl", the Scots won a school-record 26 consecutive regular season games between 1986 and 1989. Mark Reed, who quarterbacked the 1987 divisional champion team, established an NCAA Division III national record that year with 17 rushing touchdowns. Kane also coached Monmouth's first overtime game, a thrilling 13-7 victory over Knox in a 1991 snowstorm.

For the record, in the 106 seasons since Monmouth and Knox met for the first time, the Scots have played 882 football games and have won 428 victories.

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