| 1963 | Released their self-titled debut album, introducing Paddy Moloney's uilleann pipes-led sound to a folk audience well beyond Ireland's borders. |
| 1975 | Featured prominently on Stanley Kubrick's Oscar-winning 'Barry Lyndon' soundtrack, with tracks like 'Women of Ireland' anchoring the film's Irish scenes and propelling the band into mainstream recognition worldwide. |
| 1988 | Partnered with Van Morrison to record 'Irish Heartbeat', a collaboration that blended traditional uilleann pipes and whistles with Morrison's soul-inflected vocals and drew a new generation of listeners to Irish folk. |
| 1995 | 'The Long Black Veil' united the Chieftains with Mick Jagger, Sinéad O'Connor, Sting, and Ry Cooder on a single album, becoming their highest-selling record and earning them a Grammy for Best Pop Collaboration with Vocals. |
| 1996 | Won the Grammy Award for Best World Music Album for 'Santiago', which drew on centuries-old musical bonds between Ireland and Galicia recorded with the Belfast Harp Orchestra. |
| 2002 | Honored with the Lifetime Achievement Award at the BBC Radio 2 Folk Awards, recognizing four decades of bringing Carolan's harp compositions and improvisation-driven traditional Irish music to audiences across more than 50 countries. |
| 2012 | Marked their 50th anniversary with the release of 'Voice of Ages', the band's most recent studio album and a capstone to a catalog of six Grammy wins spanning folk, world music, and pop collaboration categories. |
| 2021 | Founder and uilleann pipes master Paddy Moloney died in Dublin at 83; tributes poured in from Mick Jagger, Van Morrison, Imelda May, and Irish flute legend James Galway, underscoring the global reach of the band he had led across 44 albums. |
| 2021 | Lost Paddy Moloney, who had performed on every one of the band's 44 albums; the Irish traditional music community united in a streaming funeral watched by 2,500 people online, affirming the Chieftains' irreplaceable place in Irish cultural heritage. |