[1][5] Prior to forming The Rocking Horse Winner, Gomez, Olmino and Crum had together played in the melodic hardcore band As Friends Rust.
The label compiled the songs from the band's extended play with newly recorded material to create The Rocking Horse Winner's debut album, State of Feeling Concentration, released in November 2000.
During its span, the band toured the United States several times, accompanied by such bands as Dashboard Confessional, Coheed and Cambria, The Format, Bayside, The Blood Brothers, The Weakerthans, Further Seems Forever, Midtown, Hopesfall, Hey Mercedes, Brandtson, Sense Field, Onelinedrawing, Fairweather, Koufax, Twothirtyeight, Hot Rod Circuit, Seville, The Lyndsay Diaries, The Cancer Conspiracy, Fairview, and The Remedy Session.
[7][8][9] After firing Rudas, the trio recruited vocalist Damien Moyal, shifted their style of music to melodic hardcore, and named the new band As Friends Rust in September 1996.
[13][9][14] In Red Letter Day, Crum switched to playing guitar and the band recruited drummer Darryl Bonebrake (of Vacant Andys) to complete the line-up.
[13][9][14] When Carrabba's schedule became too busy touring with Further Seems Forever in mid-1999, and Looker left to join Poison the Well, Olmino, Gomez and Crum started a second band with a new vocalist, Jolie Lindholm.
[12] Wisner had previously recorded material by many of the members' related projects, including As Friends Rust, Red Letter Day, Anchorman, Vacant Andys, and Further Seems Forever.
[19] The four songs recorded during the session, "Atmosphere", "Raspberry Water", "Elementary", and "Until Next Time", were released on a CD-R made by the band and sold at their local shows.
[15][28] This was followed by a stop at Monster Fest in Burlington, Vermont in June 2001, and four dates in North Carolina and Florida as part of the Van's Warped Tour in July 2001.
On October 13, 2001, The Rocking Horse Winner performed at Equal Vision Records' Showcase at CMJ Music Marathon, alongside other label roster bands Converge, Coheed and Cambria, Liars Academy, Fairweather, The Hope Conspiracy, and American Nightmare.
[38] The Rocking Horse Winner's sophomore full-length album, Horizon, was released on compact disc by Equal Vision Records on April 30, 2002.
The Rocking Horse Winner left Florida to tour the East Coast of the United States, on their own, for a three-week stretch that spanned from April 5–27, 2002.
[45][44] The Rocking Horse Winner then met up with Ohio-based emo band Brandtson for two week's worth of shows back up the East Coast of the United States, spanning from April 29 to May 14, 2002.
[40][46][44] After three weeks off at home, The Rocking Horse Winner took to the road again for a lengthy two-month tour of the lower 48 States, spanning from June 7 to July 30, 2002.
[46][48] After a brief week off at home, The Rocking Horse Winner was back out on the road for another month's worth of shows across the United States, spanning from August 8 to September 6, 2002.
[54][55] The music video was directed by Chris Irving, and features Dashboard Confessional's then-bass guitarist, Daniel Bonebrake, in a leading role;[16] it was released on January 28, 2003.
[62] Despite some of the band member's desire to remain home, The Rocking Horse Winner embarked on what was planned to be a two-month tour, spanning from February 2 to April 1, 2003.
[54][55][63][66] The final leg of the tour was to be shared with Missouri-based emo project The Lyndsay Diaries, for a second time going around the Southern, West Coast, Northwest and Central United States.
[54][61] On March 20, 2003, Equal Vision Records released an elusive statement from the band's publicist, Earshot Media, which wrote: "Due to extenuating circumstances, The Rocking Horse Winner has had to cancel the remainder of their tour.
"[16] Following The Rocking Horse Winner's breakup, Gomez sold off his equipment and retired from the music industry to focus on graphic design and animation.