[6] Diman received national attention in January 2018, when then-United States Representative Joe Kennedy III gave the Democratic Party's response to Donald Trump’s 2018 State of the Union Address from the school’s automotive shop.

[7] Massachusetts’s 4th congressional district, which Kennedy represented at the time, includes the school.

The Diman Regional Charter was established in 1963 to expand the area of the school's enrollment to include the surrounding towns of Somerset, Swansea and Westport, Massachusetts.

In 2013, the Diman football team won the Mayflower League Championship for the first time in school history.

The Bengals won their first round match-up against Upper Cape, but eventually lost the following week to a powerful Millis/Hopedale cooperative team.