The Tampa Bay Buccaneers have played more games against the Chicago Bears than any other team in the NFL. Viewed as a 41-season whole, that's better news for the Bears than the Buccaneers.
Tampa Bay joined the NFL in 1976 as its 27th franchise but played its first season in the AFC West, facing only AFC opponents that fall. In 1977, the Buccaneers were switched into the NFC Central, where they became twice-annual foes with the Bears (and the Packers, Lions and Vikings). It started out reasonably well, with the Bucs and Bears splitting their first four meetings…and then Chicago won 28 of the next 36.