July 19, 1986: All 4 occupants of a Cessna 421, registration number N6VR, were killed when the aircraft suffered an apparent right-hand engine failure, rolled over, and dived into a vacant lot immediately after takeoff from Addison Airport. The post-crash investigation revealed that the right-hand engine did not show any obvious signs of failure and its controls were not set to deliver full takeoff power. The crash was attributed to incorrect engine control operation; the pilot had recently purchased the Cessna 421 but had not been formally trained to fly it, and most of his twin-engined experience had been in an airplane with engine controls that operated in the reverse direction of those in the Cessna.
June 20, 1992: The pilot of a Piper J3C-65 Cub, registration number N3128M, reported trouble and attempted to return to Addison Airport soon after taking off to test a newly installed engine. While turning to line up with the runway, the airplane suddenly lost altitude, rolled upside down, and crashed in the middle of nearby Beltway Drive, killing the pilot and his passenger. The crash was attributed to breakage of the left-hand elevator control tube due to corrosion.
January 1, 2004: The pilot and passenger of a Bellanca 17-30A Super Viking, registration number N4104B, died when the aircraft struck houses in the Preston Hollow neighborhood of nearby Dallas, Texas, after departing from Addison Airport bound for Amarillo, Texas. An intense post-crash fire destroyed two houses and the remains of the Bellanca, but an elderly resident of one house escaped injury after being dragged out of the burning structure by his caregiver, who was also unhurt. The crash was attributed to spatial disorientation in densely clouded IFR conditions; the pilot had reported a partial instrument panel failure, after which radar data indicated that he was making left turns instead of right turns as directed by air traffic controllers.
October 24, 2011: A Cirrus SR22, registration number N227TX, attempted to return to Addison Airport shortly after takeoff. After several missed approaches, the aircraft crashed on a railroad track next to Hebron High School, killing one passenger and seriously injuring the pilot and a second passenger. The accident was attributed to "The pilot's failure to adequately preflight the airplane prior to departure, which resulted in a loss of engine power due to fuel exhaustion."
June 30, 2019: A Beechcraft Super King Air 350i, registration number N534FF, crashed into a hangar on airport grounds after taking off for a flight to St. Petersburg, Florida, killing all 8 passengers and 2 crew on board. The hangar was unoccupied at the time of the crash and nobody on the ground was harmed. The aircraft reportedly dropped its left wing on takeoff and immediately veered to the left. The accident is under investigation by the Federal Aviation Administration and the National Transportation Safety Board.