CHICAGO – For a second-straight year, the NFL is saying goodbye to one of the greatest quarterbacks in league history, and Bears fans are probably happy about that.

Tom Brady took to social media to announce his retirement on Wednesday, saying this time it’s “for good” as he brings his 23-year career to an end.

During his 20 years with the Patriots and three with the Buccaneers, Brady made a habit of giving opposing teams a lot of problems on the field, and the Bears were no exception.

So how did the quarterback do when facing the squad from Chicago?

(AP Photo/Ted S. Warren)

Brady finished his career against the Bears with a 6-1 record as a starter, including a perfect 5-0 mark while a member of the Patriots. In 2000, when New England traveled to Chicago, Brady was inactive in his rookie year with the team when the Bears defeated the Patriots 24-17.

His first game was a memorable one on November 10, 2002 in Champaign, the Bears’ temporary home for that season as Soldier Field was being renovated. Brady rallied the reigning Super Bowl champions from a 27-6 deficit in the second half, throwing a touchdown to David Patten with 21 seconds left to give New England a 33-30 victory.

The next match-up with the Bears would once again be a close one, this time at Gillette Stadium in Foxborough on November 26, 2006. Despite a slow offensive performance that included a pair of interceptions, Brady’s fourth quarter touchdown pass to Ben Watson was the difference in a 17-13 win.

(AP Photo/Nam Y. Huh)

The next two match-ups between Brady and the Bears were blowouts, the first coming on December 12, 2010 in a Soldier Field snowstorm. It didn’t bother the quarterback as he threw for 369 yards and two touchdowns in a 36-7 rout in Chicago.

Four years later, on October 26, 2014, it was another lopsided affair as the Patriots beat the Bears 51-23 in Foxborough, with Brady throwing five touchdown passes.

Things were a bit closer when Brady faced the Bears for the last time as a Patriot on October 21, 2018 at Soldier Field. The quarterback threw for 277 yards, three touchdowns with an interception as the Patriots held onto win 38-31.

Mitchell Trubisky’s “hail mary” completion to Kevin White on the final play of the game was stopped at the 1-yard line by New England.

(Jeff Haynes/AP Images for Panini)

Finally, in their sixth match-up against the quarterback on October 8, 2020, the Bears finally got a win against Brady, who was now a member of the Buccaneers.

Thanks to a strong defensive push from the front seven that included three sacks and eight quarterback hits, the Bears knocked off Tampa Bay 20-19. Many would remember the contest as the one where Brady lost track of downs on the Buccaneers’ final drive, which help the hosts secure the victory.

(Photo by Douglas P. DeFelice/Getty Images)

In Brady’s final game against the Bears on October 24, 2021, he returned to the form he had against the team throughout most of his career. The quarterback threw for 211 yards and four touchdowns in the Buccaneers’ 38-3 win at Raymond James Stadium.

In seven starts against the Bears, Brady completed 67 percent of his passes for 2,059 yards for 19 touchdowns compared to four interceptions. His 105.9 ranking was his fourth-highest against any opponent in the NFL.