The first game played between the two schools took place on November 6, 1897, in Amherst, Massachusetts. Massachusetts won 36–0. At the time, UMass was known as Massachusetts Agricultural College and Connecticut was officially Storrs Agricultural College. They had formed a loose association with other public colleges in New England such as present day New Hampshire and Rhode Island for the purpose of scheduling football matchups between the schools.
The colleges continued to schedule matches intermittently until after World War I, when they began to play on an almost-yearly basis through the mid-1920s. The series was discontinued until 1932, when the schools again met each year until World War II saw both universities disband their football teams. The schools would not match up again on the gridiron until Connecticut joined Massachusetts in the Yankee Conference in 1952. UConn and UMass played every season from that point on until UConn began their transition to what was then Division I-A in 2000.
UMass leads the all-time series 36–34–2. Massachusetts dominated the rivalry early, winning the first eight and 13 of the first 15 meetings between the two universities. Connecticut went on a streak of their own after that, winning 14 of the next 16 games. The 1960s again belonged to the then-Redmen of Massachusetts, as they lost only two games that decade. In the remaining years of the rivalry, the series was much more even, with neither team able to put together a winning streak of more than four games.
In April 2011, UMass announced plans to join the Mid-American Conference and move up to the NCAAFootball Bowl Subdivision, the highest level of college football in the country. Prior to this decision, the two schools had scheduled a game for August 30, 2012. UConn will play at Gillette Stadium in 2016, with UMass returning the visit to Rentschler Field in 2017.