Pinecrest offered an IB Diploma track until 2009, when the program was cancelled due to budgetary concerns and lack of student interest.

On March 12, 2021, Moore County Schools announced resumption of five day a week classes.

Pinecrest's physical plant was tailored for flexible scheduling, large and small group instruction, and independent study.

In each building a vending area that provided hot and cold foods replaced the traditional school cafeteria.

The Pinecrest curriculum offered 83 courses the first year as well as extra programs for both remediation and enrichment.

The cafeteria, also located in that building, began serving "a la carte" and regular type A school lunches.

In 1980, the Science Department expanded its college preparatory courses from five to six when it included Advanced Placement Biology.

In 1981, the Social Studies Department expanded its program to include Advanced Placement American History.

Increased attention was given to student pride, parental involvement, participation in extracurricular activities, community awareness, and continued academic excellence.

In local competition such as Quiz Bowl, Morehead nominations, and vocational contests, Pinecrest students have won more than 80% of the awards.

Community support has continued to grow, as evidenced by the passage of the 1986 School Bond Referendum which provides a $2,500,000 for construction of a new auditorium as well as other money for facility improvement.

During the 2009–2010 school year the group presented a play entitled "At the Bottom of Lake Missoula" by Ed Monk and received the top honors at the regional competition.

The show moved on to compete at the North Carolina Theatre Conference's High School Play Festival where it again took home the top prize and moved on to compete in the South Eastern Theatre Conference in Lexington, Kentucky.

This is the first time in the school's history that the theatre program has advance to the highest level of competition.

[10] In the 2013–2014 school year, the ensemble presented the Alice and Wonderland sequel titled "Through the Looking Glass".

The R. E. Lee Auditorium[14] is located on the west side of the school and houses the Band, Theatre, Orchestra, and Chorus.

Pinecrest High School has an outdoor/indoor design, with students having to traverse between outdoor classes, and some classrooms that are inside of hallways.

Also, there are benches and picnic tables set up in the courtyard allowing students the ability to sit and enjoy their lunch.

During this week, students may participate in daily events (such as Wacky Tacky Day and Blast from the Past).

The Homecoming Parade (as it is called) allows the athletes of the Football and Men's Soccer teams, Cheerleading, Marching Band and Drumline, as well as a handful of various floats designed for the event follow a circuit taking them around downtown Southern Pines.

There is generally a good turnout of observers ranging from other students, parents, friends, local business owners, as well as fans of PCHS.

Future additions include an enclosed press box, a snack bar, and a new storage building).

They defeated first round leader Providence as well as two time defending state champions Green Hope.

[citation needed] In 2008, for the first time in over 16 years, the football team defeated Richmond County High School.

In 2010, the Patriots were unable to play in playoffs due to being put on probation for on field fighting with rival Union Pines.