Holloway began as a speed skater and started cycling as practice for speed skating in the summer. His racing career began on the velodrome due to its similarities with the track. Holloway took to cycling winning his first national championship in July 2004 in the Madison. In 2005 he won his next national title at Junior Track Nationals in the 3 km Pursuit and Team Pursuit. In 2007 he took his first Criterium National title as an amateur. In 2008 he rode to 4 Elite National titles on the track. In 2010 he again won the Criterium National Title. Holloway began to race a more European focused schedule in 2011-2013 only to return to the US and race as an amateur in 2014. Holloway won 3 back-to-back Amateur Criterium Championships in 2014, 2015 and 2016, winning also the Road Race National Championship in 2016 and 2017. Towards the end of his 2017 road season Holloway shifted focus back to the track, winning 2 National Titles (Omnium and Madison) and a World Cup (Omnium) on the track in 2017 and three National Titles (Omnium, Madison, Points Race) as well as the Pan-American Madison Championship title in 2018. To date he holds 21 US National titles.
