Grassfield High School is a public high school located in Chesapeake, Virginia, USA, and is administered by Chesapeake City Public Schools. It was built to ease overcrowding at Deep Creek High School, Great Bridge High School, and Hickory High School. Grassfield, along with Western Branch High School and Oscar Smith High School, features the latest technology available in the school district. Grassfield is also the City of Chesapeake's location for the STEM (Science, Technology, Engineering, and Mathematics) school as various high school students around the city can apply for admission into the program.

By 2004 the school district was planning to spend $63.6 million to build Grassfield, and anticipated it would open in 2007.

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

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.

The football team is currently coached by Michael Biehl.

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

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

During the 2017-2018 Grassfield Swim season the girls team secured a first place victory at regionals.