The festival began in 2000, with fifteen concerts taking place in its first year. It was founded by Dave Corbett, after realising the lack of contemporary music taking place at the Edinburgh Festival. Since 2000, T on the Fringe has played host to some of the most commercially successful artists as well as the best in alternative and emerging talent. Over the years the event has seen performances by the likes of Pixies, Muse, Morrissey, Nancy Sinatra, Franz Ferdinand and Arcade Fire. The 2007 festival featured three concerts taking place at the 25,000 capacity Meadowbank Stadium, a record for the festival at the time, with the 2009 festival featuring more than fifty artists performing across seven venues.
The 2005 festival took place between 5–31 August, with more than forty acts performing across five venues. The festival's main highlight was a performance by Pixies on 28 August 2005, playing as part of their reunion tour following a 12 year hiatus. The band performed at the city's Meadowbank Stadium, the first outdoor performance for the T on the Fringe festival, with support from Idlewild and Teenage Fanclub. The festival's other main draw was two homecoming performances by Franz Ferdinand in Princess Street Gardens on 30–31 August 2005, supported by Arcade Fire. The dates were the band's first performances in the country since December the previous year. Other headline T on the Fringe shows included The Prodigy, Alabama 3, The Zutons, Weezer, Basement Jaxx and Razorlight. During August, Edinburgh's Cabaret Voltaire venue hosted a number of free concerts, featuring former Squeeze lead vocalist Glenn Tilbrook, Michael Franti, Saul Williams, Trashcan Sinatras and Rachel Fuller performing acoustic sets between the 15—26 August. Idlewild would also play acoustically at the venue, appearing on 27 August prior to supporting Pixies. Idlewild's concert was later steamed online for three months following the festival, under the moniker of "T on the Fringe Radio". The broadcast also included a feature on the Best of T Break.
The festival was deemed a success by critics, with Lynsey Hanley of The Observer stating that "..[the festival's line-up] encompassed the past, present and future of alternative rock".
2006 saw the most successful T on the Fringe in its seven year history with 100,000 tickets sold for almost 60 gigs featuring 134 artists. Snow Patrol rocked the 22,000 Meadowbank crowd in what was their biggest headline gig yet, while at the same time breaking a record already held by T on the Fringe for the biggest show at the Edinburgh Fringe. Radiohead performed at the same venue supported by Beck and Muse played the following night supported by My Chemical Romance.
 Guillemots were originally scheduled to perform at the Corn Exchange, but chose instead to play two separate smaller performances, at the City Cafe and later in the Liquid Rooms. Greg Forbes of festival website eFestivals said that Editors' supporting concert at Meadowbank Stadium "blew them away", outperforming headliners Razorlight. In 2008, The Independent reported the 2007 event had sold 130,000 tickets, highlighting that the total number of events taking place had now quadrupled from the festival's inaugural year.
Following the 2009 festival, Veronica Lee - of online newspaperguardian.co.uk - commented that a planned attempt to recreate the fringe in London was an ill-fated idea, citing Edinburgh's centric transportation system (in comparison to London's) as a reason for this.
^"Edge Festival 2009". eFestivals. 2009-08-18. Retrieved 2010-06-22. "..venues [..] including the Edinburgh Playhouse, HMV Picture House, Sneaky Pete's and Studio 24, as well as .. Cabaret Voltaire, Queen's Hall and the Corn Exchange."