Flannery's largest headlining performance in Dublin at this stage occurred at Vicar Street on 25 May 2009. He performed alongside John Spillane at Live at the Marquee in Cork on 9 July 2009. Flannery said being asked to perform there was "daunting [...] In many ways I have drifted into this career and still have to pinch myself regularly to make sure I am not imagining it all". He also performed at the Bloom Festival as part of the 50th anniversary celebrations of The Rose of Tralee in 2009. He made an appearance on the Crawdaddy Stage at Electric Picnic 2009. On 31 December 2009, he performed a date at the Cork Opera House as part of celebrations marking the end of the decade. He has sold out several other venues around Ireland and has also toured the UK.