Dugan has also made a career as a television and film director, and appears in cameo parts in many of his films. Films directed by Dennis Dugan include the 1990 comedy Problem Child (with Dugan as an All-American dad), the 2001 comedy Saving Silverman (in which Dugan plays a football referee), the 2003 comedy National Security, and the 1996 and 1999 Adam Sandler comedies Happy Gilmore (in which Dugan plays Doug Thompson, the golf tour supervisor) and Big Daddy (with Dugan as a man who reluctantly gives candy to a trick-or-treating Julian). Dugan has directed episodes of such television series as Moonlighting (was also an guest star in some episodes), Ally McBeal, and NYPD Blue.
Dugan directed The Benchwarmers, a comedy released on April 7, 2006. The film, co-produced by Adam Sandler, is about trio of men who try to make up for missed opportunities in childhood by forming a three-player baseball team to compete against standard Little League squads. Dugan himself has a bit part as Coach Bellows. Dugan directed the 2007 comedy I Now Pronounce You Chuck and Larry and You Don't Mess with the Zohan in 2008, both Adam Sandler vehicles.