| Regular Season: Week 1 |
 Chiefs |
at |
 Bears |
Sunday, September 12, 1999 |
3:00PM |
KC 17, CHI 20 |
| Regular Season: Week 2 |
 Seahawks |
at |
Bears |
Sunday, September 19, 1999 |
3:00PM |
SEA 14, CHI 13 |
| Regular Season: Week 3 |
Bears |
at |
 Raiders |
Sunday, September 26, 1999 |
3:00PM |
CHI 17, OAK 24 |
| Regular Season: Week 4 |
 Saints |
at |
Bears |
Sunday, October 3, 1999 |
3:00PM |
NO 10, CHI 14 |
| Regular Season: Week 5 |
Bears |
at |
 Vikings |
Sunday, October 10, 1999 |
3:00PM |
CHI 24, MIN 22 |
| Regular Season: Week 6 |
 Eagles |
at |
Bears |
Sunday, October 17, 1999 |
3:00PM |
PHI 20, CHI 16 |
| Regular Season: Week 7 |
Bears |
at |
 Buccaneers |
Sunday, October 24, 1999 |
3:00PM |
CHI 3, TB 6 |
| Regular Season: Week 8 |
Bears |
at |
 Redskins |
Sunday, October 31, 1999 |
2:00PM |
CHI 22, WAS 48 |
| Regular Season: Week 9 |
Bears |
at |
 Packers |
Sunday, November 7, 1999 |
3:00PM |
CHI 14, GB 13 |
| Regular Season: Week 10 |
Vikings |
at |
Bears |
Sunday, November 14, 1999 |
3:00PM |
MIN 27, CHI 24 |
| Regular Season: Week 11 |
Bears |
at |
 Chargers |
Sunday, November 21, 1999 |
3:00PM |
CHI 23, SD 20 |
| Regular Season: Week 12 |
Bears |
at |
 Lions |
Thursday, November 25, 1999 |
3:00PM |
CHI 17, DET 21 |
| Regular Season: Week 13 |
Packers |
at |
Bears |
Sunday, December 5, 1999 |
3:00PM |
GB 35, CHI 19 |
| Regular Season: Week 15 |
Lions |
at |
Bears |
Sunday, December 19, 1999 |
3:00PM |
DET 10, CHI 28 |
| Regular Season: Week 16 |
Bears |
at |
 Rams |
Sunday, December 26, 1999 |
3:00PM |
CHI 12, STL 34 |
| Regular Season: Week 17 |
Buccaneers |
at |
Bears |
Sunday, January 2, 2000 |
3:00PM |
TB 20, CHI 6 |