| Rk | Day | Date | Tm | Opp | Tm | Opp | |||
|---|---|---|---|---|---|---|---|---|---|
| 1 | Sun | September 12, 1999 | W | Dallas Cowboys | @ | Washington Redskins | 41 | 35 | box |
| 2 | Mon | September 20, 1999 | W | Dallas Cowboys | Atlanta Falcons | 24 | 7 | box | |
| 3 | Sun | October 3, 1999 | W | Dallas Cowboys | Arizona Cardinals | 35 | 7 | box | |
| 4 | Sun | October 10, 1999 | L | Dallas Cowboys | @ | Philadelphia Eagles | 10 | 13 | box |
| 5 | Mon | October 18, 1999 | L | Dallas Cowboys | @ | New York Giants | 10 | 13 | box |
| 6 | Sun | October 24, 1999 | W | Dallas Cowboys | Washington Redskins | 38 | 20 | box | |
| 7 | Sun | October 31, 1999 | L | Dallas Cowboys | @ | Indianapolis Colts | 24 | 34 | box |
| 8 | Mon | November 8, 1999 | L | Dallas Cowboys | @ | Minnesota Vikings | 17 | 27 | box |
| 9 | Thu | November 25, 1999 | W | Dallas Cowboys | Miami Dolphins | 20 | 0 | box | |
| 10 | Sun | December 5, 1999 | L | Dallas Cowboys | @ | New England Patriots | 6 | 13 | box |
| 11 | Sun | December 12, 1999 | W | Dallas Cowboys | Philadelphia Eagles | 20 | 10 | box | |
| 12 | Sun | December 19, 1999 | L | Dallas Cowboys | New York Jets | 21 | 22 | box | |
| 13 | Fri | December 24, 1999 | L | Dallas Cowboys | @ | New Orleans Saints | 24 | 31 | box |
| 14 | Sun | January 2, 2000 | W | Dallas Cowboys | New York Giants | 26 | 18 | box | |
| 15 | Sun | January 9, 2000 | L | Dallas Cowboys | @ | Minnesota Vikings | 10 | 27 | box |