1999 New Orleans Saints season

The 1999 New Orleans Saints season was the Saints' thirty-third season in the National Football League (NFL). This was Mike Ditka's third and final season as the Saints' head coach, as he was fired, along with his entire coaching staff and general manager Bill Kuharich, three days after the conclusion of the season.

During 1999, the Saints became the first team to lose to the expansion Cleveland Browns and in the process became the only team since the NFL/AFL merger in 1970 to lose to the last winless team in successive seasons.

NFL Draft
With the only pick in the draft the New Orleans Saints selected running back Ricky Williams out of the University of Texas with the fifth overall pick. The Saints traded all of their draft picks in the 1999 draft in order to move up so they could draft Williams, as well as a first round pick in the 2000 NFL Draft that eventually was used by the Washington Redskins to draft LaVar Arrington.

Week 1: vs. Carolina Panthers
With the win, the Saints started 1–0 for the second season in a row. However, this would be New Orleans' last win for two months.

Week 4: at Chicago Bears
The Saints had a 10–0 lead with just under 2 minutes left to play, but saw the lead quickly fade away. The Bears scored their first points of the game with 1:48 left in the 4th on a 22-yard pass from Shane Matthews to wide receiver Curtis Conway. Chicago would recover the onside kick and go down the field in 61 seconds to win 14–10 after scoring the game-winning touchdown with just 6 seconds left to play.

Week 8: vs. Cleveland Browns
For week 8, the 1–5 Saints hosted the 0–7 Browns, who were playing in their first season since 1995 following a relocation controversy that saw the franchise officially being deactivated for three seasons.

The Saints would take a 16–14 lead with 0:21 left in the game. On the final play of the game, Cleveland quarterback Tim Couch heaved a Hail Mary pass into the end zone that was tipped by several New Orleans defenders before being caught by Browns wide receiver Kevin Johnson as the clock struck 0:00, giving Cleveland its first win since December 17, 1995.

The Saints' offense finished the game with 351 yards of total offense and controlled the ball for 40:50, while the Brown's offense only had 243 total yards and a possession time of 19:10. However, New Orleans committed five turnovers, two of which gave Cleveland a short field that resulted in touchdowns for the Browns.

With the loss, the Saints fell to 1–7 and their losing streak was extended to six games. Additionally, the Saints became the first team to lose to the expansion Browns and lost to the last winless team in the NFL, having lost to the 0–7 Carolina Panthers during week 9 of the previous season. This also marked the second time an expansion franchise got its first win over New Orleans, as the Tampa Bay Buccaneers, who started 0–26, got its first win as a franchise by defeating the Saints 33–14 during the 1977 season.

Week 10: vs. San Francisco 49ers
With the win, the Saints improved to 2–7 and snapped a seven game losing streak that lasted for just over two months.