| 1987 | Red Rider, the Canadian rock group he fronted, claimed the Juno Award for Group of the Year, capping several years of well-received albums and establishing Cochrane as one of Canada's most prominent rock voices. |
| 1991 | Released the solo album "Mad Mad World" featuring the global smash "Life Is a Highway," which hit number 1 in Canada, number 6 on the US Billboard Hot 100, and drove the album to Diamond certification in Canada for over one million copies sold. |
| 1992 | "Mad Mad World" swept four Juno Awards including Album of the Year, Single of the Year, Male Vocalist of the Year, and Songwriter of the Year, while "Life Is a Highway" earned a Grammy nomination for Best Male Rock Vocal Performance. |
| 1995 | Delivered "Ragged Ass Road" on the EMI label, the second of several solo full-lengths through the decade that kept him a consistent presence on Canadian rock radio. |
| 2003 | Inducted into the Canadian Music Hall of Fame for outstanding contribution to Canadian music, with Jeff Healey presenting the honor at the Juno Awards; Cochrane closed the ceremony performing a medley joined onstage by host Shania Twain for 'Life Is a Highway.' |
| 2015 | Released "Take It Home," his most recent studio album, sustaining a solo discography that stretches from the early '90s through the 2010s. |
| 2016 | Issued a 25th-anniversary edition of "Mad Mad World," marking a quarter century since the album that made 'Life Is a Highway' an enduring rock standard with over one billion streams. |
| 2022 | Honored with the SOCAN Cultural Impact Award for 'Life Is a Highway' at the 33rd Annual SOCAN Awards, with Rush's Alex Lifeson presenting the recognition for a song that has accumulated over one billion streams and dozens of major licensing deals. |
| 2022 | Toured extensively across Canada supporting "Take It Home," with stops in Mission, Ottawa, Kingston, Calgary, and Winnipeg among others. |
| 2024 | Appeared on a multi-artist bill in Toronto alongside Blue Rodeo and Sarah McLachlan, affirming his place in the canon of classic Canadian rock. |