|1999 San Diego Chargers season|
|Head coach||Mike Riley|
|General manager||Bobby Beathard|
|Home field||Qualcomm Stadium|
|Division place||3rd AFC West|
|Playoff finish||did not qualify|
The 1999 San Diego Chargers season began with the team trying to improve on their 5–11 record in 1998. It was Mike Riley's first season as the team's head coach. Before the season, Ryan Leaf wound up suffering a shoulder injury during the Chargers' first training camp and was lost for the season. Following a 4-1 start, the team suffered six straight losses before winning four of their final five games to finish 8-8.
|1999 San Diego Chargers staff|
Special teams coaches
Strength and conditioning
|1999 San Diego Chargers final roster|
|2||September 19, 1999||at Cincinnati Bengals||W 34–7||
|3||September 26, 1999||Indianapolis Colts||L 27–19||
|4||October 3, 1999||Kansas City Chiefs||W 21–14||
|5||October 10, 1999||at Detroit Lions||W 20–10||
|6||October 17, 1999||Seattle Seahawks||W 13–10||
|7||October 24, 1999||Green Bay Packers||L 31–3||
|8||October 31, 1999||at Kansas City Chiefs||L 34–0||
|9||November 7, 1999||Denver Broncos||L 33–17||
|10||November 14, 1999||at Oakland Raiders||L 28–9||
|11||November 21, 1999||Chicago Bears||L 23–20||
|12||November 28, 1999||at Minnesota Vikings||L 35–27||
|13||December 5, 1999||Cleveland Browns||W 23–10||
|14||December 12, 1999||at Seattle Seahawks||W 19–16||
|15||December 19, 1999||at Miami Dolphins||L 12–9||
|16||December 26, 1999||Oakland Raiders||W 23–20||
|17||January 2, 2000||at Denver Broncos||W 12–6||
|(3) Seattle Seahawks||9||7||0||.563||338||298||L1|
|Kansas City Chiefs||9||7||0||.563||390||322||L2|
|San Diego Chargers||8||8||0||.500||269||316||W2|
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