The 1990s were a decade of transition for the Bears, starting out within their competitive window and closing out having made two head coaching changes.
Mike Ditka and the much of the defensive core of the '85 champs were still holding together in 1990, a year in which they went 11-5, and won the NFC Central before falling to the Giants in the divisional playoffs. They lost in the wild card round in 1991, and then the bottom fell out with consecutive fourth-place divisional finishes the next two seasons.
With that, Ditka was out, an era at it's end after he posted a coaching record of 106 and 62 in his eleven memorable campaigns. And in came Dave Wannstedt, the much-sought-after defensive coordinator of the Super Bowl champion Dallas Cowboys. Wannstedt led the Bears to a 9-7 record and a playoff spot in 1994. They defeated the Vikings in the wild card game before falling to the 49ers in the next round, and it would be their final postseason appearance of the decade. Wannstedt was replaced by Dick Jauron after his six seasons in charge culminated with consecutive 4-12 records.
The 1990's not only saw the retirements of their legendary stars of the '80s, but they closed on a mournful note when Walter Payton died on November 1st, 1999. The greatest player in franchise history, gone far too soon at just age 45.