| Regular Season: Week 1 |
 Giants |
at |
 Buccaneers |
Sunday, September 12, 1999 |
3:00PM |
NYG 17, TB 13 |
| Regular Season: Week 2 |
Buccaneers |
at |
 Eagles |
Sunday, September 19, 1999 |
3:00PM |
TB 19, PHI 5 |
| Regular Season: Week 3 |
 Broncos |
at |
Buccaneers |
Sunday, September 26, 1999 |
3:00PM |
DEN 10, TB 13 |
| Regular Season: Week 4 |
Buccaneers |
at |
 Vikings |
Sunday, October 3, 1999 |
3:00PM |
TB 14, MIN 21 |
| Regular Season: Week 5 |
Buccaneers |
at |
 Packers |
Sunday, October 10, 1999 |
3:00PM |
TB 23, GB 26 |
| Regular Season: Week 7 |
 Bears |
at |
Buccaneers |
Sunday, October 24, 1999 |
3:00PM |
CHI 3, TB 6 |
| Regular Season: Week 8 |
Buccaneers |
at |
 Lions |
Sunday, October 31, 1999 |
2:00PM |
TB 3, DET 20 |
| Regular Season: Week 9 |
Buccaneers |
at |
 Saints |
Sunday, November 7, 1999 |
3:00PM |
TB 31, NO 16 |
| Regular Season: Week 10 |
 Chiefs |
at |
Buccaneers |
Sunday, November 14, 1999 |
3:00PM |
KC 10, TB 17 |
| Regular Season: Week 11 |
 Falcons |
at |
Buccaneers |
Sunday, November 21, 1999 |
3:00PM |
ATL 10, TB 19 |
| Regular Season: Week 12 |
Buccaneers |
at |
 Seahawks |
Sunday, November 28, 1999 |
3:00PM |
TB 16, SEA 3 |
| Regular Season: Week 13 |
Vikings |
at |
Buccaneers |
Monday, December 6, 1999 |
3:00PM |
MIN 17, TB 24 |
| Regular Season: Week 14 |
Lions |
at |
Buccaneers |
Sunday, December 12, 1999 |
3:00PM |
DET 16, TB 23 |
| Regular Season: Week 15 |
Buccaneers |
at |
 Raiders |
Sunday, December 19, 1999 |
3:00PM |
TB 0, OAK 45 |
| Regular Season: Week 16 |
Packers |
at |
Buccaneers |
Sunday, December 26, 1999 |
3:00PM |
GB 10, TB 29 |
| Regular Season: Week 17 |
Buccaneers |
at |
Bears |
Sunday, January 2, 2000 |
3:00PM |
TB 20, CHI 6 |
| Divisional Playoffs: Week 19 |
 Redskins |
at |
Buccaneers |
Saturday, January 15, 2000 |
3:00PM |
WAS 13, TB 14 |
| Conference Championship: Week 20 |
Buccaneers |
at |
 Rams |
Sunday, January 23, 2000 |
3:00PM |
TB 6, STL 11 |