It is a part of the Highland Park Independent School District, which serves approximately 32,200 residents who are predominantly college-educated professionals and business leaders.

[5] In 2003, a four-year remodeling of the school was completed that added a new wing to provide more classroom space and allow for a new, larger cafeteria.

In 2015, a $361.4 million bond package passed HPISD board approval and citizens' vote[18] that allowed for new parking spaces and renovations to the attached tennis center and natatorium—eventually eliminating the natatorium and replacing it with classrooms.

In 1999, Dallas police issued 200 alcohol and curfew violation citations to Park Cities teens partying in a Deep Ellum warehouse.

[20] In 2004, Simon & Schuster published Francine Pascal's The Ruling Class, a teen drama set at Highland Park High School.

[21] In 2005, The Dallas Morning News published a story about the Friday of Highland Park's homecoming spirit week, on which several seniors dressed as thugs, Mexicans, maids, and other caricatures of racial minorities.

Some pointed to this as support for the general perception of HPHS and the Park Cities as a "bubble" (as the area is known in the Dallas-Fort Worth Metroplex).

In 2005 and 2006, Highland Park students received a multitude of state and national awards and set several new records in Texas.

[22] The UIL Science Team, under the leadership of AP Chemistry teacher Wenzen Chuang, won state for the second time in school history.

[24] The books were The Art of Racing in the Rain, by Garth Stein; The Working Poor: Invisible in America, by David K. Shipler; Siddhartha, by Hermann Hesse; The Absolutely True Diary of a Part-Time Indian, by Sherman Alexie; An Abundance of Katherines, by John Green; The Glass Castle, by Jeannette Walls; and Song of Solomon, by Toni Morrison.

"[25] In 2015, Orr retired and was replaced by Tom Trigg, who had previously served as the superintendent of Blue Valley Unified School District in Overland Park, Kansas.

[29] 86.0% of HPHS graduates in 2015 were rated college-ready in both English language arts and mathematics by the TEA compared to a state average of 35.0%.

[5] After graduation, 94% of the class of 2016 matriculated to a four-year college, including Harvard, Stanford, West Point, and Air Force.

A 2011 The Dallas Morning News report stated that 93% of HPHS students were "college-ready" (ready to attend post-secondary educational institutions).

[35] The baseball team's games are held at Scotland Yard (Highland Park), immediately north of the high school campus.

The Highland Park girls' swimming and diving team holds the UIL record with ten consecutive state titles.

In 1995, the Highland Park men's gymnastics team won state with Burton Rhodes finishing 1st in the Floor event.

In the 1920s, Bryan Street High School players called the HPHS football team the "silk stocking boys."

[11]Coached by Rusty Russell (1942–45) and led by Doak Walker and Bobby Layne, the Scots made it to the championship game in 1944 and 1945.

After losing 20-7 to Port Arthur in 1944, Highland Park tied Waco 7-7 in the 1945 state championship in front of a record 45,790-person crowd at the Cotton Bowl,[39] becoming co-champion.

[40][41] Allen received the 2013 Grant Teaff Fellowship of Christian Athletes Lifetime Achievement Award, joining such coaching greats as Tony Dungy and Bobby Bowden.

The team beat Marshall 59-0, the largest margin of victory ever in a UIL 11-man state championship football game.

In 2017, the Scots won the Division I 5A state final against Manvel Prep High School, 53-49 on December 22 in front of 24,975 people at AT&T Stadium.

In 2018, Highland Park won its third straight state championship in a game against Shadow Creek and completed a perfect 16-0 record.

The Highland Park girls' cross country team has set numerous records, sending a runner to the state meet every year since the program was created.

Other rivals include Jesuit College Preparatory School of Dallas (another Dallas-based team), which beat HPHS in the 2016 and 2017 DI title games.

Highland Park holds the UIL record for most athletic state titles by one school[citation needed]: 77 (in all classes).

The event has become an annual festival where HPHS students have enjoyed meeting, working with, and learning from distinguished writers, including George Plimpton, Doug Wright, Michael Chabon, Marion Winik, Scott Simon, Tim O'Brien, Russell Banks, Anchee Min, Billy Collins, Tobias Wolff, and Jamie Ford.

[67] In the September 1981 issue of Money Magazine, Highland Park was ranked as one of the top twelve public high schools in the United States; in January 1984, Parade Magazine listed Highland Park as among the top fifteen schools in the United States.

[68] In 2008, Highland Park was ranked 15th in Newsweek Magazine's list of the top public high schools in the United States,[69] based on the Challenge Index by Jay Mathews.