[5] Grassfield's 24 varsity sports teams compete in Conference 2 of the VHSL's Group 6A South Region.

[6] In November 2007 Grassfield held a home run derby to raise money for their athletic teams.

(*) Nansemond River High School forfeited their victory due to an ineligible player.

[9] (**) VHSL moved the 2020 season from autumn to spring and reduced the number of games played due to COVID-19 restrictions.

In February 2009 the Grassfield wrestling team secured 1st place for the regular season and won Southeastern District tournament title.

[12] In its first year, the Grassfield High School Drama Department collected many awards for its performances.

[12] Grassfield has consistently held one of the top theatre departments in the region, winning 1st place in the VHSL Southeast District competition thirteen years consecutively, and once the reorganization of VHSL, the theatre company has been the Conference 2 champion, regional champion in 2014, and garnered VHSL State Championships for Region 6A in 2014 with their production of "King Midas and the Golden Touch" as well as their original play "Digital Breadcrumbs" in 2016.

The Singers of Grassfield High School received a rating of superior in their inaugural year, and are a participants in various other performances in Chesapeake and Southeastern Virginia.

The Grassfield High School Orchestra Program is in its 15th year of existence, and is made up of three main performing groups that span approximately 216 students.

The group consists of members of the Grassfield Fine Arts Department, and is focused on performing popular and rock tunes for audiences.