| Rk | Day | Date | Tm | Opp | Tm | Opp | |||
|---|---|---|---|---|---|---|---|---|---|
| 1 | Sun | September 19, 1999 | L | Cleveland Browns | @ | Tennessee Titans | 9 | 26 | box |
| 2 | Sun | September 26, 1999 | L | Cleveland Browns | @ | Baltimore Ravens | 10 | 17 | box |
| 3 | Sun | October 3, 1999 | L | Cleveland Browns | New England Patriots | 7 | 19 | box | |
| 4 | Sun | October 10, 1999 | L | Cleveland Browns | Cincinnati Bengals | 17 | 18 | box | |
| 5 | Sun | October 17, 1999 | L | Cleveland Browns | @ | Jacksonville Jaguars | 7 | 24 | box |
| 6 | Sun | October 24, 1999 | L | Cleveland Browns | @ | St. Louis Rams | 3 | 34 | box |
| 7 | Sun | October 31, 1999 | W | Cleveland Browns | @ | New Orleans Saints | 21 | 16 | box |
| 8 | Sun | November 7, 1999 | L | Cleveland Browns | Baltimore Ravens | 9 | 41 | box | |
| 9 | Sun | November 14, 1999 | W | Cleveland Browns | @ | Pittsburgh Steelers | 16 | 15 | box |
| 10 | Sun | November 21, 1999 | L | Cleveland Browns | Carolina Panthers | 17 | 31 | box | |
| 11 | Sun | November 28, 1999 | L | Cleveland Browns | Tennessee Titans | 21 | 33 | box | |
| 12 | Sun | December 5, 1999 | L | Cleveland Browns | @ | San Diego Chargers | 10 | 23 | box |
| 13 | Sun | December 12, 1999 | L | Cleveland Browns | @ | Cincinnati Bengals | 28 | 44 | box |
| 14 | Sun | December 19, 1999 | L | Cleveland Browns | Jacksonville Jaguars | 14 | 24 | box |