Fall - Cheerleading, Boys and GirlsCross Country, Field Hockey, Football, Boys and Girls Golf, Boys and Girls Volleyball, Marching Band
Winter - Boys and Girls Basketball, Cheerleading, Gymnastics, Boys and Girls Indoor Track, Boys and Girls Swimming and Diving, Wrestling, Winter Guard, and Crew
Spring - Baseball, Boys and Girls Tennis, Boys and Girls Soccer, Softball, Boys Lacrosse, and Boys and Girls Outdoor Track
In November 2007 Grassfield held a home run derby to raise money for their athletic teams. It included B.J. Upton, Justin Upton, Ryan Zimmerman, David Wright, Michael Cuddyer, and Mark Reynolds. The Girls Varsity Volleyball team made school history in their fall 2008 season by winning both the regular season and district tournament titles, and receiving the first district championship banner in the gym.
Football
The football team is currently coached by Martin Asprey.
During the 2017-2018 Grassfield Swim season the girls team secured a first place victory at regionals.
Wrestling
In February 2009 the Grassfield wrestling team secured 1st place for the regular season and won Southeastern District tournament title. During February, they finished 2nd in the Eastern Regional Tournament and 4th at the AAA state tournament. In 2009, the Grizzlies had 2 state champions: Caleb Richardson in the class and Andrew Clement in the class.
In its first year, the Grassfield High School Drama Department collected many awards for its performances. Some awards include Second place at the state level for VHSL Theatre competition, best actor awards and best ensemble from the Greek play "Medea". In their second year, The Grassfield Theater Company travelled to the VTA and got second place in the state, first in districts regionals and state for VHSL, winning two best actor awards and first place overall for their production of John Steinbeck's The Pearl. 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.
Choral department
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. All three of Grassfield High School's choirs, the Select Women's Treble Singers, Chamber Singers, Concert Singers and Freshmen Choir all received a rating of superior in their second year of existence. The Select women's and Chamber are the honors chior that are more evolved in competition and harder music. Select is more superior than chamber.
Concert band
In their inaugural year, both the Grassfield High School Freshman and Upperclassmen Concert bands received superior ratings at VBODA District IV band festival. In their second year, the Freshman and Upperclassmen Concert bands received ratings of excellent, and the newly created Symphonic Band received a Superior rating. This gave Grassfield the title of Virginia All-State honors band, for receiving Superior ratings for their Marching and top-ranked Concert bands. In 2019 the Symphonic Band and Concert band both received superior ratings.
