Simmonds was very successful as a junior. He reached the final with the Junior Davis Cup team in 2002. In the same year he won the Orange Bowl doubles competition . 2003 came the title at the Australian Open , which he won with Scott Oudsema . Two more times he was in doubles at a Grand Slam tournament in the semi-finals. In the junior world rankings he reached 2nd place in early 2004.
In 2005 he began playing tournaments with the professionals on a regular basis. This year he mainly played tournaments on the ITF Future Tour and the ATP Challenger Tour , and thanks to a wildcard he also got his first appearance on the ATP World Tour in Washington . He finished his first year as a professional at 339th place in the world rankings . 2006 was his most successful year. In addition to his first individual Future title, he also triumphed at the Challenger in León . In the final, he defeated Dick Norman . In addition, he often made it into the Challenger quarter-finals, so that he was in October 2006 with 219th place on his career high. Previously, Simmonds played at the US Open against Richard Gasquet, his only single match at a Grand Slam tournament; in doubles he lost next to this year in 2004 and 2007 each in the first round.
In 2007 and 2008, the American did not manage to win more than one match at any Challenger. So he fell out of the top 400 in the world. Things went better for him in doubles and in June 2007 he reached his career record with 200th place. In 2007 and 2008 he won his two only Challengers in doubles. In total, he had three futures titles in singles and six in doubles in his career. After Simmonds was no longer listed in the top 500 players in 2009 and 2010, he was able to surprise a little again in 2011 when he qualified for the ATP tournament in Atlanta . There he was defeated by Lleyton Hewitt . Most recently, he mainly played in futures before ceasing regular gaming operations in 2012. In 2015 he came back for three tournaments until he finally ended his career.