All-Time Record: Raiders lead series 8-7 (.533)
2019 record: 8-8
Division Finish: (3rd/NFC North)
Playoffs: None
Head Coach: Matt Nagy
Key additions: TE Cole Kmet, DB Jaylon Johnson, LB Danny Trevathan, QB Nick Foles, LB Robert Quinn, TE Jimmy Graham, WR Ted Ginn Jr., LB Barkevious Mingo
Notable players: QB Mitchell Trubisky, WR Allen Robinson, LB Khalil Mack, LB Roquan Smith, DB Eddie Jackson, DB Kyle Fuller, DT Akiem Hicks, RB Tarik Cohen, NT Eddie Goldman
Key losses: LB Leonard Floyd, CB Prince Amukamara, LB Nick Kwiatkoski, TE Trey Burton, S Ha Ha Clinton-Dix, WR Taylor Gabriel, G Kyle Long, QB Chase Daniel
• Raiders and Bears first matchup came in 1972.