Simon Andrews began his racing career on this 16th birthday in 1999, securing pole position and second place in his first race in the New Era Club Championship. He went on to compete in several British Supersport Championship “shoot outs” for newcomers in 2000 as well as achieving a win and five podiums in the New Era Club Championships.

After a top ten finish in the Honda Hornet Cup in 2001, Simon remained in the British Supersport Championship for the next few seasons, securing multiple pole positions and podium finishes. In 2003 he also contested the AXO European Superstock Championship an the British Superstock Championship. In 2006, Simon was the only British rider to compete in both the British Supersport Championship and the British Superbike Championship and finish consistently in the top ten.

In 2007, Andrews made the step up to British Superbikes full-time, finishing 16th overall. In 2008, he finished eight scoring 176 points and was awarded top Yamaha rider for the year scoring the most points for the Factory. In 2009, Andrews signed with the official Kawasaki BSB team and also made his debut in road racing, becoming the fastest newcomer at the Macau World street race. He also competed in the final race of the World Endurance Championship with Phase One.

2010 and 2011 saw Andrews continue with Kawasaki in BSB. He also made his debut in the Isle of Man TT and became the 2011 fastest newcomer. In 2012, Simon joined the Honda TT Legends team, contesting the 2012 World Endurance Championship, the Isle of Man TT and the Northwest 200. He was forced to miss of the latter half of the season following a serious crash during the Isle of Man TT Superbike race, but re-joins the team for the EWC races in 2013.