The Jacksonville Jaguars and Chicago Bears played each other in the regular season and playoffs 8 times in league history. Jacksonville Jaguars 3 games and Chicago Bears won 5 games in their all-time meeting here listed below.
Chicago Bears leading the all-time series 5-3-0.
| Where | When | Result |
| Chicago Bears @ Jacksonville Jaguars | 12/27/2020 | 41-17 (Bears) |
| Jacksonville Jaguars @ Chicago Bears | 10/16/2016 | 17-16 (Jaguars) |
| Chicago Bears @ Jacksonville Jaguars | 10/07/2012 | 41-3 (Bears) |
| Jacksonville Jaguars @ Chicago Bears | 12/07/2008 | 10-23 (Bears) |
| Chicago Bears @ Jacksonville Jaguars | 12/12/2004 | 3-22 (Jaguars) |
| Jacksonville Jaguars @ Chicago Bears | 01/06/2002 | 13-33 (Bears) |
| Jacksonville Jaguars @ Chicago Bears | 09/06/1998 | 24-23 (Jaguars) |
| Chicago Bears @ Jacksonville Jaguars | 10/15/1995 | 30-27 (Bears) |
