The 1999 Chicago Bears entered a new era under first-year head coach Dick Jauron, looking to shake off the doldrums of back-to-back four-win campaigns. The franchise laid a foundation through the draft by selecting quarterback Cade McNown in the first round, while adding immediate defensive contributors in Russell Davis, Marty Booker, Warrick Holdman, Rosevelt Colvin, and Jerry Azumah. On the offensive line, free-agent tackle Blake Brockermeyer was brought in to bolster protection. Despite these changes, the product on the field resulted in a 6-10 record, placing Chicago fifth in the competitive NFC Central Division and extending their playoff drought.

Statistically, the offense presented a fascinating contrast. Chicago ranked 8th in total yards gaining 5,523 and 3rd in passing yards with 4,136, driven by a league-leading 684 pass attempts. However, efficiency lagged, as they finished 25th in total points scored with 272 (17.0 ppg). The signal-caller duties were split among Shane Matthews (3-4 record, 1,645 yards, 10 TDs), rookie Cade McNown (2-4 record, 1,465 yards, 8 TDs), and Jim Miller (1-2 record, 1,242 yards, 7 TDs). Wide receiver Marcus Robinson enjoyed a stellar breakout season, hauling in 84 receptions for 1,400 yards and 9 touchdowns. He was complemented by Bobby Engram, who registered 88 catches for 947 yards. The ground game remained stagnant, ranking 26th in rushing yards gained with 1,387 as Curtis Enis led all rushers with 916 yards on 287 carries.

Chicago's defense struggled to contain opponents consistently, ranking 20th in points allowed coneding 341 (21.3 ppg) and 29th in total yards allowed surrendering 5,704. Middle linebacker Barry Minter anchored the defense, leading the roster with 122 combined tackles, 3.0 sacks, and a interception returned for a touchdown. Strong safety Tony Parrish hit the century mark with 105 tackles. The pass rush generated 37 total sacks, powered by veteran defensive end Clyde Simmons who notched 7.0 sacks, interior tackle Jim Flanigan who brought down opposing QB's 6.0 times, and defensive end Bryan Robinson who logged 5.0 sacks. Cornerback Walt Harris led the secondary in breakups with 14 passes defended, while safety Chris Hudson paced the team with three interceptions.

The season was defined by extreme swings. Chicago started 3-2, highlighted by a thrilling 24-22 road victory against the Minnesota Vikings in Week 5. Following a three-game losing streak, they bounced back in Week 9 to snap a 10-game losing streak against the rival Green Bay Packers with a 14-13 victory at Lambeau Field. After a dramatic 23-20 overtime win against the San Diego Chargers in Week 11 brought them to 5-6, the team sputtered down the stretch, dropping four of their final five games. That late-season slide included a 35-19 return loss to Green Bay and a 34-12 defeat against the eventual Super Bowl champion St. Louis Rams.

Missing the postseason for the fifth consecutive year, the 1999 Bears served as an important transition year. While the record reflected a rebuilding roster, individual highlights emerged. Marcus Robinson's 1,400 receiving yards established a single-season franchise record at the time, earning him votes for Comeback Player of the Year. Running back Glyn Milburn provided elite special teams production, accumulating 1,426 kickoff return yards and 346 punt return yards to secure Pro Bowl and First-Team All-Pro selections. These performances, along with the development of the 1999 draft class, planted the seeds for the franchise's eventual division title two years later.