Summary
Jolliff Middle is a 6–8 middle school in Chesapeake, VA, serving 753 students as part of Chesapeake City Public Schools, a district ranked 34th out of 131 in Virginia. The school has earned a 4-star rating for four straight years and currently ranks 104th out of 416 Virginia middle schools, placing it in the top quarter statewide. Notably, Jolliff has maintained strong results even as the share of students eligible for free/reduced-price meals jumped to 73.8% — a level of economic need that would typically weigh on test scores. Chronic absenteeism stands at just 8.0%, well below the district rate of 11.1% and barely half the state's 14.8%.
Academically, Jolliff's signature strength is math. Eighth-grade math proficiency was 74.7% in 2025–2026, well above the district's 62.4% and the state's 46.9%. Students who accelerate into advanced courses do exceptionally well, with 100% proficiency in Geometry and Algebra I for multiple consecutive years. Reading scores exceed state averages in all three grade levels, and 8th grade science proficiency (73.5%) also tops the state. In 6th grade civics and economics, 79.4% of students were proficient, compared to 69.4% statewide. The one area to watch is 7th grade math (54.3%), though the previous year's class posted 77.5%, suggesting variation between cohorts rather than a systemic issue.
Compared to nearby schools, Jolliff stands out. It outperforms Crestwood Middle, Oscar Smith Middle, and Deep Creek Middle — all of which serve similar poverty levels — and it is far ahead of Portsmouth's Churchland Middle, Cradock Middle, and William E. Waters Middle, where 8th grade math proficiency ranges from just 24% to 31%. Even Hugo A. Owens Middle, a higher-income school ranked 59th statewide, trails Jolliff in 8th grade math (66.9% vs. 74.7%). The school also invests more per student ($12,110) than most Chesapeake-area middle schools and has a favorable 11.5:1 student-teacher ratio. Two areas for potential improvement: military-connected students rank below the school's overall profile, and outcomes for students with disabilities have slipped from a high point in 2022–2023.
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