| 6-10 | Missed Playoffs |
| Record | Outcome |
The Chicago Bears finished the regular season with a 6-10 record. They went 3-5 at home and 3-5 on the road.
No, the Bears didn't make the Playoffs in 1999.
The Chicago Bears finished the regular season with a point differential of -69. Based on their point differential and their pythagorean expectation, the Bears could have been expected to have about 5.9 wins.
In close, one-score games, the 1999 Chicago Bears went 5-6. In games decided by a field goal or less, the Bears went 4-3.
During the regular season, the 1999 Chicago Bears went 1-1 in overtime games.
| Week | Date | Opponent | Score | |
|---|---|---|---|---|
| 1 | Sun, Sep 12, 1999 Sun, Sep 12 | vs Kansas City Chiefs Chiefs | Win W 20 - 17 | |
| 2 | Sun, Sep 19, 1999 Sun, Sep 19 | vs Seattle Seahawks Seahawks | Loss L 13 - 14 | |
| 3 | Sun, Sep 26, 1999 Sun, Sep 26 | @ Oakland Raiders Raiders | Loss L 17 - 24 | |
| 4 | Sun, Oct 3, 1999 Sun, Oct 3 | vs New Orleans Saints Saints | Win W 14 - 10 | |
| 5 | Sun, Oct 10, 1999 Sun, Oct 10 | @ Minnesota Vikings Vikings | Win W 24 - 22 | |
| 6 | Sun, Oct 17, 1999 Sun, Oct 17 | vs Philadelphia Eagles Eagles | Loss L 16 - 20 | |
| 7 | Sun, Oct 24, 1999 Sun, Oct 24 | @ Tampa Bay Buccaneers Buccaneers | Loss L 3 - 6 | |
| 8 | Sun, Oct 31, 1999 Sun, Oct 31 | @ Washington Redskins Redskins | Loss L 22 - 48 | |
| 9 | Sun, Nov 7, 1999 Sun, Nov 7 | @ Green Bay Packers Packers | Win W 14 - 13 | |
| 10 | Sun, Nov 14, 1999 Sun, Nov 14 | vs Minnesota Vikings Vikings | Loss L 24 - 27 | OT |
| 11 | Sun, Nov 21, 1999 Sun, Nov 21 | @ San Diego Chargers Chargers | Win W 23 - 20 | OT |
| 12 | Thu, Nov 25, 1999 Thu, Nov 25 | @ Detroit Lions Lions | Loss L 17 - 21 | |
| 13 | Sun, Dec 5, 1999 Sun, Dec 5 | vs Green Bay Packers Packers | Loss L 19 - 35 | |
| 15 | Sun, Dec 19, 1999 Sun, Dec 19 | vs Detroit Lions Lions | Win W 28 - 10 | |
| 16 | Sun, Dec 26, 1999 Sun, Dec 26 | @ St. Louis Rams Rams | Loss L 12 - 34 | |
| 17 | Sun, Jan 2, 2000 Sun, Jan 2, 2000 | vs Tampa Bay Buccaneers Buccaneers | Loss L 6 - 20 | |
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