The band, originally called Periwinkle, came together in the suburbs in 1997 at the Sydney Grammar School when 15-year-olds Dave Rennick and Hugh Boyce were joined by Alex Moore and English-born Tim Derricourt. The line-up has occasionally expanded on stage to include keyboardists Mark Bradshaw and later Ned Cooke who is now a permanent member of the band.
The band played at various all ages shows and charity benefits until they reached legal age to play in the licensed venues which are the focus of Sydney's rock scene. The band members moved to the inner suburbs of Sydney and after various name changes settled on Dappled Cities Fly, chosen because its inappropriateness as a band name made them laugh at the time although the band "have regretted it ever since".
Dappled Cities Fly have enjoyed and helped foster the revival since 2000 of Sydney's live music scene and the opening of several new venues. The band have made several extensive tours of Australia and toured New Zealand in 2004. In 2006 the band performed in London and at various shows in the United States, including SXSW, where they played again in 2009. They also regularly headline their own shows, very often at the Hopetoun Hotel, with bills showcasing new local groups. Their frequent live shows drew a regular following of fans and the band became popular supporting international acts touring eastern Australia.
The band's several early single and EP releases were critically well received and played Australia-wide on various radio stations. Their first album, A Smile, after several years in the making, was released in late 2004 and featured as album of the week on radio stations FBi and Triple J, in most of the Sydney street press and in various other media. The Sydney Morning Herald reviewer Bernard Zuel wrote of A Smile that it "weaves between lo-fi indie rock, oddly bent pop and a kind of big-emotion, big-gesture music that seems refracted through a vaguely hallucinogenic mirror".
In 2006 their second album Granddance, which was recorded at various studios in Los Angeles, was released. The album's cover artwork has the band's name as Dappled Cities, without the word "Fly"; however as Tim Derricourt explained to The Drum Media magazine, this was done mainly for artistic reasons, and does not amount to a formal name change for the band. Although this was accurate at the time, they have officially dropped the Fly from their moniker as of 2009, simply calling themselves Dappled Cities. In late 2007 the band recorded and released a cover version of "November Rain", played with local Sydney band Red Riders, with whom they had toured earlier in the year.
On February 27, 2008, a bulletin was posted on the band's MySpace announcing that Hugh Boyce had left the band to pursue a career in biomechanical engineering. In the following months, the band announced the arrival of their new drummer, Allan Kumpulainen.
Dappled Cities' latest album, Zounds, was released on Speak 'n Spell in Australia on August 15, 2009, awaiting a North American release on Dangerbird Records a month later on September 15. The band are touring Australia in support of the album, and have released a single titled "The Price".