The 1988 Dallas Cowboys season was the final year for Cowboys head coach Tom Landry. After the season, the team underwent drastic changes including a new head coach, and change of ownership from Bum Bright to current owner Jerry Jones. Notable additions to the team in 1988 included wide receiver Michael Irvin, linebacker Ken Norton Jr. and defensive tackle Chad Hennings. It was the first time since 1976 that future hall-of-fame running back Tony Dorsett was not on the Dallas roster. Dorsett had been relegated to a backup role to Herschel Walker for most of 1987 and was traded to the Denver Broncos during the offseason.
The 1988 season faced hardship from the release of the schedule. In 1987, Dallas had finished at 7–8, in a 3-way tie for second place in the NFC East and tiebreaking rules gave Dallas the "second place position", even though Dallas finished fifth (last) in the NFC East in 1987 in "union games" (i.e. a strong replacement team had inflated the Boys' '87 record). As a result, their 1988 schedule was primarily against teams that were strong in 1987 (and also in 1988).
Steve Pelluer had won the starting quarterback job from veteran Danny White late in the 1987 season and won the job in training camp for 1988. Early in the season, White appeared briefly in relief roles before suffering a season-ending injury in week 7, which elevated Kevin Sweeney to the backup position. Sweeney briefly took over the starting job for Pelluer in weeks 11 and 12, but the results were poor and Pelluer regained the job.
In the season opener, Dallas lost to Pittsburgh, 24–21. The Cowboys had the ball inside the Pittsburgh 10 in the game's closing seconds (in position to tie or win) but Steve Pelluer was intercepted. After a close win over Phoenix in week two, Dallas lost to the New York Giants, 12–10 (the margin of defeat being a strange safety on the opening kickoff). A last-second goal line stand brought victory over Atlanta in week four but the following week, the Cowboys lost to New Orleans on a last-second Morten Andersen field goal. Two convincing losses followed and at 2–5, the season was in jeopardy.
In week 8, Dallas traveled to Philadelphia. Bad blood still existed from 1987, when Philadelphia coach Buddy Ryan had (in the game's closing seconds) called a deep pass play while already leading by 10. The Cowboys roared to a 20–0 lead in the first half, but the Eagles came back to win 24–23 by scoring a touchdown on the game's final play. The next week, Dallas blew a 10–0 second-half lead to lose to the Phoenix Cardinals and fell to 2–7. Five more losses followed (and the losing streak extended to 10 games) before Dallas upset the defending Super Bowl champion Washington Redskins in Week 15 in RFK Stadium (eliminating the Redskins from playoff contention). The Redskins win marked the end of an era (and Landry's last win) but was also a harbinger as rookie (and future hall-of-fame) wide receiver Irvin caught three touchdown passes. The team lost the next week at Texas Stadium to Philadelphia and finished 3–13, the worst record in the entire NFL and the team's worst record since 1960, when they were an expansion team. A bright spot for the season was Walker, who led the NFC in rushing yards.
In addition to Landry, this was also the final season for long-time Cowboys such as president-general manager Tex Schramm, personnel director Gil Brandt, defensive tackle Randy White, quarterback Danny White, linebacker Mike Hegman, and defensive coordinator Ernie Stautner.