With this lineup, they toured, playing at London clubs and appearing as the supporting act for the likes of the Pogues (then named Pogue Mahone) and Bad Manners, mostly playing covers of rockabilly tunes. However, they soon lost both female guitarists, and Boz Boorer took over playing the guitar for their shows. Phil Bloomberg managed the group.
After gaining a substantial club following and some press coverage, they signed a record deal with CBS Records, a move which Halpin later regretted:
“It was not particularly what I wanted to because I can’t stand majors. I would have gone for an independent like Rough Trade and keep more control over what we were gonna do. The records we did with CBS were not really what I would have wanted them to have been.”
Tensions arose when recording the first single, "Give Me My Freedom". CBS felt the final result wasn't commercial enough and so it was re-done with a different producer, losing, Halpin later commented, the band’s original sound in the process. In addition, CBS refused to allow Boz Boorer to be a full band member, not letting him appear on the single cover or in interviews or video clips.
Despite all these problems, "Give Me My Freedom" was released in April, 1984. The group had some press coverage and also did some television shows (most notably The Tube) and a John Peel session at Radio One. The Shillelagh Sisters also went on tour as the supporting act for British rock band Spear of Destiny. However, all this promotion did not lead to pop success and their single charted poorly at #100 in the UK charts in May, 1984.
Soon after, CBS released their second single, the Latin-flavoured "Passion Fruit", with a cover of Nancy Sinatra’s "These Boots Are Made For Walkin'" as the B-side. The record was remixed by pop mogul Pete Waterman. It failed to gain any interest and didn’t make the UK top 100, peaking in the 140s.
The band's dissatisfaction with the way CBS was marketing them, along with differences between the band members, led to the band's demise in late 1984.
In 1986 Trisha O'Flynn became part of the female group Coming Up Roses (created by two ex-members of cult band Dolly Mixture), playing the saxophone, but it didn't last long and she, alongside Leigh Luscious (guitar) and Claire Kenny (bass), left the band. The band did not release any records while she was part of it.
In 1988 Jacquie O’Sullivan joined girl band Bananarama, where she enjoyed several UK top 40 hits (including 2 top 5 hits). After promoting a Greatest Hits album and releasing a studio album, she left the group for good in late 1991. She then formed the group Slippry Feet with friend Paul Simper.
Lynder Halpin married Boz Boorer and played in some indie bands.
Around this time, an official website, www.shillelaghsisters.co.uk, featuring a discography and an interview with Lynder, was assembled, but it soon vanished.
A third album from Jacquie O’Sullivan, tentatively titled “The Jacquie O Collection”, featuring new songs and re-recordings of her hits with Bananarama, was announced but the label folded and nothing was released.