| 1999 Dallas Cowboys season | |
|---|---|
| Owner | Jerry Jones |
| General manager | Jerry Jones |
| Head coach | Chan Gailey |
| Home field | Texas Stadium |
| Results | |
| Record | 8–8 |
| Division place | 2nd NFC East |
| Playoff finish | Lost Wild Card Playoffs (at Vikings) 10–27 |
| Pro Bowlers | RB Emmitt Smith CB Deion Sanders LB Dexter Coakley OL Larry Allen OT Erik Williams |
The 1999 season was the Dallas Cowboys' 40th in the National Football League (NFL) and second and final under head coach Chan Gailey. The Cowboys were looking to return to the playoffs, improve on their 10–6 record from the previous season and head to the Super Bowl for the final time in the 1990s.
While the Cowboys were unable to repeat as division champions or match their win total from 1998, their 8–8 record enabled them to qualify for the playoffs as a wild-card team. The Cowboys lost to the Minnesota Vikings 27–10, ending their season in the opening round of the playoffs for a second consecutive year.
Gailey was fired at the end of the season. The Cowboys would not return to the playoffs until 2003.