| Regular Season: Week 1 |
 Cowboys |
at |
 Redskins |
Sunday, September 12, 1999 |
3:00PM |
DAL 41, WAS 35 |
| Regular Season: Week 2 |
 Falcons |
at |
Cowboys |
Monday, September 20, 1999 |
3:00PM |
ATL 7, DAL 24 |
| Regular Season: Week 4 |
 Cardinals |
at |
Cowboys |
Sunday, October 3, 1999 |
3:00PM |
ARI 7, DAL 35 |
| Regular Season: Week 5 |
Cowboys |
at |
 Eagles |
Sunday, October 10, 1999 |
3:00PM |
DAL 10, PHI 13 |
| Regular Season: Week 6 |
Cowboys |
at |
 Giants |
Monday, October 18, 1999 |
3:00PM |
DAL 10, NYG 13 |
| Regular Season: Week 7 |
Redskins |
at |
Cowboys |
Sunday, October 24, 1999 |
3:00PM |
WAS 20, DAL 38 |
| Regular Season: Week 8 |
Cowboys |
at |
 Colts |
Sunday, October 31, 1999 |
2:00PM |
DAL 24, IND 34 |
| Regular Season: Week 9 |
Cowboys |
at |
 Vikings |
Monday, November 8, 1999 |
3:00PM |
DAL 17, MIN 27 |
| Regular Season: Week 10 |
 Packers |
at |
Cowboys |
Sunday, November 14, 1999 |
3:00PM |
GB 13, DAL 27 |
| Regular Season: Week 11 |
Cowboys |
at |
Cardinals |
Sunday, November 21, 1999 |
3:00PM |
DAL 9, ARI 13 |
| Regular Season: Week 12 |
 Dolphins |
at |
Cowboys |
Thursday, November 25, 1999 |
3:00PM |
MIA 0, DAL 20 |
| Regular Season: Week 13 |
Cowboys |
at |
 Patriots |
Sunday, December 5, 1999 |
3:00PM |
DAL 6, NE 13 |
| Regular Season: Week 14 |
Eagles |
at |
Cowboys |
Sunday, December 12, 1999 |
3:00PM |
PHI 10, DAL 20 |
| Regular Season: Week 15 |
 Jets |
at |
Cowboys |
Sunday, December 19, 1999 |
3:00PM |
NYJ 22, DAL 21 |
| Regular Season: Week 16 |
Cowboys |
at |
 Saints |
Friday, December 24, 1999 |
3:00PM |
DAL 24, NO 31 |
| Regular Season: Week 17 |
Giants |
at |
Cowboys |
Sunday, January 2, 2000 |
3:00PM |
NYG 18, DAL 26 |
| Wild Card: Week 18 |
Cowboys |
at |
Vikings |
Sunday, January 9, 2000 |
3:00PM |
DAL 10, MIN 27 |