| 1965 | Broke out of Winnipeg onto the international stage with "Shakin' All Over," putting Canadian rock on the global map before the band had even settled on a permanent lineup. |
| 1969 | "These Eyes," written by Burton Cummings and Randy Bachman, became the band's first American hit, crossing over from Canada and cracking the US Top 10. |
| 1970 | "American Woman" hit number one on the Billboard Hot 100, the first Canadian act ever to top the American chart, and stayed there for three weeks, with the riff born from a broken guitar string at an Ontario gig the year before. |
| 1975 | Disbanded following the commercial peak of the early 1970s, with Burton Cummings and Randy Bachman each departing to successful solo and side-project careers including Bachman-Turner Overdrive. |
| 1987 | Original members Cummings, Bachman, Kale, and Peterson were inducted into the Canadian Music Hall of Fame at the Juno Awards, recognizing their foundational role in Canadian rock. |
| 2011 | Recorded three new original songs in the studio, the first new Guess Who material in years, and began rotating them into live performances on the band's ongoing world tour. |
| 2023 | Burton Cummings and Randy Bachman filed a $20 million lawsuit against former bandmates Jim Kale and Garry Peterson, alleging the touring band was falsely implying the founders were still performing. |
| 2024 | Cummings and Bachman settled the trademark dispute, reacquiring the Guess Who name and ending a bitter multi-decade legal battle over who could tour as the band. |
| 2026 | Launched the "Takin' It Back" North American tour, the duo's first U.S. dates together as The Guess Who in 23 years, kicking off at Mystic Lake Amphitheater with support from Eagles guitarist Don Felder. |