| Jan. 8 | The Chargers advanced to the AFC Championship game with a 22-21 victory over the Miami Dolphins in front of a record home crowd of 63,381. San Diego recovered from a 21-6, third- quarter deficit. |
| Jan. 15 | The Chargers advanced to the Super Bowl for the first time in franchise history with a stunning, 17-13 victory over the heavily-favored Pittsburgh Steelers at Three Rivers Stadium. Linebacker Dennis Gibson knocked down a Neil O'Donnell pass and stopped the Steelers on downs on the Chargers' three-yard line with 1:04 left in the game. The team returned to San Diego following the game and were greeted by an estimated crowd of 70,000 screaming fans in San Diego Jack Murphy Stadium. |
| Jan. 29 | In Super Bowl XXIX in Miami, Florida, the Chargers suffered a 49-26 loss to the San Francisco 49ers. |
| Jan. 30 | More than 100,000 San Diegans crowded the streets of downtown San Diego at a post-Super Bowl parade to show support for the Chargers upon their return from Miami. |
| Feb. 1 | Defensive Coordinator Bill Arnsparger retired. |
| March 6 | Chargers President/Vice Chairman Dean Spanos announces that the team has come to an agreement with the City of San Diego to extend its lease and call San Diego home through the year 2020. As part of the agreement, plans were outlined to permanently expand the seating capacity of San Diego Jack Murphy Stadium to accommodate more than 70,000 fans and modernize the 28-year-old facility. |
| May 2 | Chargers President/Vice Chairman Dean Spanos signed General Manager Bobby Beathard and Head Coach Bobby Ross to contract extensions through the 1999 season. |
| May 18 | Alex Spanos announced plans to create the Alex G. Spanos San Diego Foundation, a nonprofit organization designed to "help San Diego build on its strengths by supporting individuals, activities and organizations that work to make the city a better place to live." In addition, he announced the donation of $1.5 million to the San Diego Hall of Champions. |
| June 19 | Linebacker David Griggs was killed in a one-car accident in Davie, Florida, becoming the first player in team history to die while on the active roster. |
| July 29 | Former Chargers tight end Kellen Winslow is inducted into the Pro Football Hall of Fame. |
| Aug. 19 | San Diego's preseason game at Houston is cancelled due to an "unsafe" playing surface at the Houston Astrodome. It was the first time an NFL game has been cancelled. |
| Sept. 3 | The Chargers become the first team to play a regular-season game versus the Raiders at the Oakland Coliseum since 1981. |
| Nov. 27 | Dwayne Harper ties a team record with three interceptions in a 12-6 win over the Raiders. |
| Dec. 17 | John Carney becomes the team's all-time field goal leader when he kicks his 147th and 148th career field goals with the Chargers in a 27-24 win at Indianapolis. Carney surpassed Rolf Benirschke's record of 146. |
| Dec. 23 | Shaun Gayle returns an interception 99 yards through a barrage of snowballs thrown by fans as the Chargers seal a 27-17 win over the Giants at the New Jersey Meadowlands. It marks the Chargers fifth-consecutive win and gives San Diego its third playoff berth in the past four seasons. |
| Dec. 31 | The Chargers lose to the Indianapolis Colts, 35-20, in a Wild Card playoff game, ending San Diego's hope of returning to its second consecutive Super Bowl. |