The 2019 season was the Oakland Raiders' 60th since they were founded, their 50th in the National Football League (NFL) and their second under head coach Jon Gruden since his rehiring by the organization (sixth overall).

[3] Prior to the season, the Raiders hired former NFL Network draft guru and former Notre Dame Football on NBC color commentator Mike Mayock as general manager.

[7] The team briefly negotiated for sharing Levi's Stadium with the 49ers, but the proposal was reportedly rejected for costing more than the Coliseum's asking price.

[8][10] As part of the lease agreement, the Raiders did not receive naming rights revenue from RingCentral, and game-day expenses for the Coliseum Authority would also be capped.

On March 27, Green Bay Packers President Mark Murphy stated during the league owners' meetings that the Packers and Raiders were in negotiations to play a preseason game August 22 at Investors Group Field in Winnipeg, Manitoba, with the Raiders as the designated home team.

[17] When the preseason schedule was released, the August 22 Packers-Raiders game was subtly noted as a neutral-site contest, with no location identified.

Just days before the game, the Raiders released wide receiver Antonio Brown, who was acquired via trade prior to the season, stemming from conduct detrimental to the team, including a heated argument with general manager Mike Mayock.

[24] Linebacker Vontaze Burfict was ejected from the game and later suspended the rest of the season for initiating two helmet-to-helmet hits, including one on Colts tight end Jack Doyle.

Like the previous week, Oakland surged to an early lead, this time behind strong play from Josh Jacobs.

Chicago took the lead in the third quarter with 21 unanswered points, but the Raiders eventually answered with a rushing touchdown from Jacobs with just under two minutes left in the game.

Despite holding a 16–6 lead late in the fourth quarter, Oakland allowed a touchdown pass from Jaguars quarterback Gardner Minshew to Chris Conley, then failed to run out the clock and missed the subsequent field goal attempt.

[28][29] With their fourth straight loss, the Raiders fell to 6–8, but remained in the playoff hunt as the Pittsburgh Steelers would lose later that night.

This was the Chargers' final home game at Dignity Health Sports Park before moving into their new stadium in the 2020 season.

With the win, the Raiders snapped their 4-game losing streak, improving to 7–8 and keeping their slim playoff hopes alive.