| Sport: | football |
| Year: | 1999 |
| Team: | UMass Minutemen |
| Conference: | Atlantic 10 Conference |
| Short Conf: | A-10 |
| Record: | 9–4 |
| Conf Record: | 8–1 |
| Hc Year: | 2nd |
| Dc Year: | 2nd |
| Champion: | A-10 champion |
| Bowl: | NCAA Division I-AA Quarterfinal |
| Bowl Result: | L 21–38 vs. Georgia Southern |
The 1999 UMass Minutemen football team represented the University of Massachusetts Amherst in the 1999 NCAA Division I-AA football season as a member of the Atlantic 10 Conference. The team was coached by Mark Whipple and played its home games at Warren McGuirk Alumni Stadium in Hadley, Massachusetts. The Minutemen entered the season with high expectations as defending National Champions, but struggled out of the gate as they lost three of their first four games. UMass turned its fortune around after that, using a 77–0 thrashing of to propel it on an eight-game winning streak. The Minutemen did not lose again until the second round of the NCAA Playoffs against the eventual champions, Georgia Southern. UMass finished the season with a record of 9–4 overall and 8–1 in conference play.