After West Point, Pressler was the head coach at Ohio Wesleyan University (OWU). In October 2007, he was inducted into the Ohio Wesleyan University Hall of Fame. During his 5-year tenure at OWU from 1986 through 1990, Pressler amassed a 69–16 record, four NCAC championships, five visits to the NCAA Division III semi-finals, three NCAA Division III Championship game appearances, 29 All-American selections, and five NCAA Division III players of the year. His contributions to the OWU lacrosse program made him the winningest coach (.812) in OWU's over 50-year lacrosse history.
Pressler was hired by Bryant University to lead their lacrosse team in 2007. In June 2022, Pressler announced his retirement from coaching.
After his retirement, Pressler was announced as the head coach for Highland Park High School's lacrosse program. In his first season at the helm, he led the Scots to a Texas High School Lacrosse League Class AA state championship.[10]
He was fired in 2006 in the wake of allegations of rape against three athletes in the program that proved to be baseless. Pressler's firing was publicly portrayed by Duke as a resignation, which gave rise to the implication that the coach resigned due to the students' presumed guilt.[citation needed] Pressler believed the players were innocent and had argued that the lacrosse season should not be canceled until the DNA test results were returned.[12] Pressler has written (with co-author Don Yaeger) a book giving his view of the incident, It's Not About the Truth: The Untold Story of the Duke Lacrosse Rape Case and the Lives It Shattered.
Pressler demanded compensation from Duke for wrongful termination. In early June 2007, Pressler and Duke agreed upon a financial settlement for an undisclosed amount.[13][14]
Then in October 2007, Pressler filed suit against Duke, alleging the university broke the terms of the confidential settlement. Pressler asserted that Duke broke the terms of the settlement when he was slandered by Duke senior vice president John Burness, who made disparaging comments about him, saying the difference between Pressler and the current lacrosse coach was "night and day." The suit sought to void the settlement and to pursue damages in a trial rather than by arbitration, as specified in his contract.[15]
The trial judge ruled for Pressler's claims, and was upheld by the Court of Appeals on September 1, 2009.
Pressler's obligation to submit his claims to arbitration was voided by the June settlement. Pressler was free to proceed with his suit, including discovery.[16] On March 31, 2010, the final day before discovery would start, Duke settled with Pressler. Although terms of the settlement were not disclosed, Duke issued an apology.[17]
National champion
Postseason invitational champion
Conference regular season champion
Conference regular season and conference tournament champion
Division regular season champion
Division regular season and conference tournament champion
Conference tournament champion