1999 Dallas Cowboys season

The 1999 Dallas Cowboys season would mark their 40th in the NFL.

Hall of Fame Game

 * Cleveland Browns 20, Dallas Cowboys 17 (Overtime)

Regular season
The season would begin at Washington with a dramatic come-from-behind victory over the hated division rival Washington Redskins. After trailing by three touchdowns in the second half, free agent acquisition Rocket Ismail would pay immediate dividends for the team by hauling in the winning touchdown catch in overtime while Troy Aikman would throw for a franchise record five touchdowns in a single game (since matched by Tony Romo).

The team would start out strong with a 3–0 record, but a week 4 injury to wide receiver Michael Irvin against the Philadelphia Eagles eventually forced him into retirement. Afterwards, Dallas would struggle down the stretch as age and injury would begin to take its toll. The team would again make the playoffs despite an 8–8 season, but would lose once more in the first round to the Minnesota Vikings. Despite leading the team to consecutive playoff berths and seemingly re-igniting the Dallas offense, owner Jerry Jones would fire head coach Chan Gailey after the season.

Notable additions to the team was fan favorite linebacker Dat Nguyen, the only (to date) Vietnamese-American to play in the NFL.

This marked the final season for future hall-of-famer Michael Irvin and longtime Cowboys fullback Daryl "Moose" Johnston. Irvin and Johnston both suffered season ending (and as it turned out career ending) injuries early in the season. Irvin was the last Cowboys player to have played for Tom Landry.