The initial line-up was Jan Hellriegel (guitar/vocals), Megan Miller (guitar), Venessa Anich (drums), Felicity "Flick" Rhind (bass) and Sarah McNabb (backing vocals, percussion). In 1986 Megan Miller was replaced by Leanne Ibell when Miller left for work reasons, and in 1988 Zan Wright replaced Sarah McNabb.

After recording the song 'Replacements' for the 1986 National Student Radio compilation Weird Culture Weird Custom, the band chose to not use the southern recording studios, moving north to Auckland in December 1987.

They released two EPs Private Wasteland (1988) and Your Estimation (1990) on Wellington indie Jayrem Records, but both the recordings were done in Auckland. Their first EP was recorded at Mascot Studios with Victor Grbic and the second at The Lab with Terry Moore.

The first EP was partially funded by a late 1987 $500 grant from the Ministry Of  Women's Affairs, who also gave the band a further grant to live on for two years - all except Jan Hellriegel who was working at her father's panel shop in West Auckland by then and did not qualify. 

Cassandra’s Ears enjoyed playing the numerous local Dunedin venues and they also got on the road and toured nationwide, including a 1989 tour with Straitjacket Fits, but they never released a full-length album. After five years together, Jan Hellriegel left the band and signed to Warner Music as a solo artist, releasing the successful albums It's My Sin (1992) and Tremble (1995).

Although their recorded output was small, in 2010 the two Cassandra’s Ears EPs were released on CD for the first time to create their first full-length album The Cassandra’s Ears Story. The songs were re-ordered to make a coherent listen and remastered by Steve McGough at Stebbing Studios. The band reformed for one night (Saturday November 6, 2010) to launch their CD Cassandra’s Ears Story at The King's Arms in Auckland.