Before coaching the Norfolk Admirals to their worst finish in franchise history, Stirling spent a season and a half as coach of the New York Islanders before his dismissal in January 2006, though he led the Islanders to an impressive record of 38–29–11–4 in his first season as an NHL head coach. In the NHL playoffs, the Islanders were beaten by the eventual Stanley Cup-winning Tampa Bay Lightning in five games.
Stirling has also played centre for various teams in the NCAA, AHL and NAHL. He was the firsthead coach of the Bridgeport Sound Tigers, where he led Bridgeport to a Regular Season title in his first season. He also coached the Springfield Falcons, Babson College and Providence College and as assistant coach of the Islanders and the Lowell Lock Monsters. While in college, Stirling never had a losing season. He is also one of the few people to coach at three different levels of NCAA hockey.
After the disappointing season with the Admirals, general manager Jay Feaster announced that Stirling would not be the coach heading into the 2008–09 AHL season. Stirling was given a job as a scout for the team. On June 16, 2008, the German DEL club Iserlohn Roosters announced that Stirling had signed a two-year contract as its head coach. After 44 games and an 0–6 series, he was dismissed by the Roosters on February 5, 2009.
Stirling was signed as an assistant coach of the Binghamton Senators (the Ottawa Senators' farm team) in 2009. The Binghamton Senators won the AHL's Calder Cup one season later.
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