| Team: | San Diego Chargers |
| Year: | 1999 |
| Record: | 8–8 |
| Division Place: | 3rd AFC West |
| Coach: | Mike Riley |
| General Manager: | Bobby Beathard |
| Owner: | Alex Spanos |
| Stadium: | Qualcomm Stadium |
| Playoffs: | Did not qualify |
| Shortnavlink: | Chargers seasons |
The 1999 season was the San Diego Chargers' 30th in the National Football League (NFL), their 40th overall and their first under head coach Mike Riley.
During the Chargers’ first training camp in preseason, quarterback Ryan Leaf suffered a shoulder injury and missed the entire season. Following a 4–1 start, the Chargers suffered six straight losses before winning four of their final five games to finish 8–8.
See main article: article and 1999 NFL draft.
| Week | Date | Opponent | Result | Record | Venue | Attendance | |
|---|---|---|---|---|---|---|---|
| 1 | Bye | ||||||
| 2 | September 19 | at Cincinnati Bengals | W 34–7 | 1–0 | Cinergy Field | 47,660 | |
| 3 | September 26 | Indianapolis Colts | L 19–27 | 1–1 | Qualcomm Stadium | 56,942 | |
| 4 | October 3 | Kansas City Chiefs | W 21–14 | 2–1 | Qualcomm Stadium | 58,099 | |
| 5 | October 10 | at Detroit Lions | W 20–10 | 3–1 | Pontiac Silverdome | 61,481 | |
| 6 | October 17 | Seattle Seahawks | W 13–10 | 4–1 | Qualcomm Stadium | 59,432 | |
| 7 | October 24 | Green Bay Packers | L 3–31 | 4–2 | Qualcomm Stadium | 68,274 | |
| 8 | October 31 | at Kansas City Chiefs | L 0–34 | 4–3 | Arrowhead Stadium | 78,473 | |
| 9 | November 7 | Denver Broncos | L 17–33 | 4–4 | Qualcomm Stadium | 61,204 | |
| 10 | November 14 | at Oakland Raiders | L 9–28 | 4–5 | Network Associates Coliseum | 43,353 | |
| 11 | November 21 | Chicago Bears | L 20–23 | 4–6 | Qualcomm Stadium | 56,055 | |
| 12 | November 28 | at Minnesota Vikings | L 27–35 | 4–7 | Hubert H. Humphrey Metrodome | 64,232 | |
| 13 | December 5 | Cleveland Browns | W 23–10 | 5–7 | Qualcomm Stadium | 53,147 | |
| 14 | December 12 | at Seattle Seahawks | W 19–16 | 6–7 | Kingdome | 66,318 | |
| 15 | December 19 | at Miami Dolphins | L 9–12 | 6–8 | Pro Player Stadium | 73,765 | |
| 16 | December 26 | Oakland Raiders | W 23–20 | 7–8 | Qualcomm Stadium | 63,846 | |
| 17 | January 2 | at Denver Broncos | W 12–6 | 8–8 | Mile High Stadium | 69,278 | |
| Note: Intra-division opponents are in bold text. | |||||||