1999 San Diego Chargers season

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.