No. 5 – December 13, 1999 @ Jacksonville Jaguars
Broncos 24, Jaguars 27

For the third straight year, the Denver Broncos played a Monday Night Football game in December, and for the third straight year they suffered defeat. But there was no silver lining for this loss, as there had been in the two years prior.

Entering the game at 4-9, Denver’s back-to-back Super Bowl victory hangover was in full effect. Terrell Davis had been out since Week 4 with a torn ACL, and while Olandis Gary still rushed for 1,159 yards in his absence, the loss of both Davis and Elway was catastrophic.

Quarterback Brian Griese struggled out of the gate and missed three starts in November due to injury. He was not much better in his December return following the bye, losing his first game back against Kansas City, followed by this heartbreaker to the Jags.

After staking a 14-point lead early in the second quarter, Denver needed a late fourth-quarter drive by Griese to tie the game at 24 with under 2:00 to play. But Mark Brunell did just enough to get Jacksonville into field goal range and Mike Hollis kicked a 23-yarder as time expired to send Denver home with a 4-9 record and many, many questions.