The district is classified by the New Jersey Department of Education as being in District Factor Group "J", the-highest of eight groupings. District Factor Groups organize districts statewide to allow comparison by common socioeconomic characteristics of the local districts. From lowest socioeconomic status to highest, the categories are A, B, CD, DE, FG, GH, I and J.
The West Windsor-Plainsboro Regional School District was the result of the 1969 merger of two separate, neighboring school districts - the Plainsboro School District and the West Windsor School District - as both towns were starting to grow rapidly. The districts merged so that they could accommodate the increasing number of students newly enrolling.
With a decline in the number of student athletes playing football at WW-P South that would be inadequate for the school to field a team of its own, the district attempted to combine the teams from the two schools to have them operate as a single co-operative football team for the 2017-18 school year based at South HS. Given that the size of the schools is larger than the threshold established by the state for co-op programs (North is classified as Group III and South as Group IV, based on the size of the enrollment of each school), the proposal was rejected by the West Jersey Football League and by the Leagues and Conferences Committee of the New Jersey State Interscholastic Athletic Association, before an appeal of the decision was rejected by the Commissioner of the New Jersey Department of Education. In August 2017, the district announced that WW-P North would cancel its program. The members of the canceled program will be eligible to play for the North junior varsity football team, but will not be able to play for the South team.
The West Windsor-Plainsboro Regional School District is one of the top achieving districts in New Jersey. The high schools have held first to fifth places in many of the state's rankings. In 2004, West Windsor-Plainsboro High School North was ranked #1 in the state of New Jersey by New Jersey Monthly magazine and West Windsor-Plainsboro High School South was ranked #5. West Windsor-Plainsboro High School South was the 9th ranked public high school, and North was 18th-ranked, in New Jersey out of 316 schools statewide, in New Jersey Monthly magazine's September 2006 cover story on the state's Top Public High Schools.