| Regular Season: Week 1 |
 Steelers |
at |
 Browns |
Sunday, September 12, 1999 |
3:00PM |
PIT 43, CLE 0 |
| Regular Season: Week 2 |
Browns |
at |
 Titans |
Sunday, September 19, 1999 |
3:00PM |
CLE 9, TEN 26 |
| Regular Season: Week 3 |
Browns |
at |
 Ravens |
Sunday, September 26, 1999 |
3:00PM |
CLE 10, BAL 17 |
| Regular Season: Week 4 |
 Patriots |
at |
Browns |
Sunday, October 3, 1999 |
3:00PM |
NE 19, CLE 7 |
| Regular Season: Week 5 |
 Bengals |
at |
Browns |
Sunday, October 10, 1999 |
3:00PM |
CIN 18, CLE 17 |
| Regular Season: Week 6 |
Browns |
at |
 Jaguars |
Sunday, October 17, 1999 |
3:00PM |
CLE 7, JAC 24 |
| Regular Season: Week 7 |
Browns |
at |
 Rams |
Sunday, October 24, 1999 |
3:00PM |
CLE 3, STL 34 |
| Regular Season: Week 8 |
Browns |
at |
 Saints |
Sunday, October 31, 1999 |
2:00PM |
CLE 21, NO 16 |
| Regular Season: Week 9 |
Ravens |
at |
Browns |
Sunday, November 7, 1999 |
3:00PM |
BAL 41, CLE 9 |
| Regular Season: Week 10 |
Browns |
at |
Steelers |
Sunday, November 14, 1999 |
3:00PM |
CLE 16, PIT 15 |
| Regular Season: Week 11 |
 Panthers |
at |
Browns |
Sunday, November 21, 1999 |
3:00PM |
CAR 31, CLE 17 |
| Regular Season: Week 12 |
Titans |
at |
Browns |
Sunday, November 28, 1999 |
3:00PM |
TEN 33, CLE 21 |
| Regular Season: Week 13 |
Browns |
at |
 Chargers |
Sunday, December 5, 1999 |
3:00PM |
CLE 10, SD 23 |
| Regular Season: Week 14 |
Browns |
at |
Bengals |
Sunday, December 12, 1999 |
3:00PM |
CLE 28, CIN 44 |
| Regular Season: Week 15 |
Jaguars |
at |
Browns |
Sunday, December 19, 1999 |
3:00PM |
JAC 24, CLE 14 |
| Regular Season: Week 16 |
 Colts |
at |
Browns |
Sunday, December 26, 1999 |
3:00PM |
IND 29, CLE 28 |