New York Red Bulls

Richards was drafted in the second round of the 2007 MLS SuperDraft by New York Red Bulls, establishing himself as the first team right winger for the club. On 5 May 2007, Richards scored his first MLS regular season goal in a 3–3 tie at Real Salt Lake. He concluded his first MLS season appearing in 28 matches, including 27 starts, in which he managed two goals and six assists. His assist total was second on the club and led all league rookies. At the conclusion of the season Richards was selected as one of three nominees for league rookie of the year honours.

Richards appeared in 23 MLS regular season matches in 2008, scoring 3 goals and recording 6 assists. In the 2008 MLS Cup Playoffs, Richards helped the Red Bulls to an upset over defending Champion Houston Dynamo (4-1 on aggregate). Richards tallied the club's first goal in a 3-0 rout in the second leg of the series in Robertson Stadium in Houston. He also drew a penalty and assisted on the third goal. In 2009, Richards appeared in 27 league matches scoring 3 goals.

On 20 March 2010, Richards scored the third goal for Red Bulls in a 3-1 victory against Santos FC, which was the first match played at the new Red Bull Arena.^[2][3] On 25 July 2010, Richards scored a goal in helping lead New York to a 2-1 victory against Manchester City in a friendly match.^[4] On 24 September 2010, Richards appeared in his 100th league match for New York and helped lead the club to a 2-0 victory in The Home Depot Center over Los Angeles Galaxy scoring his team's first goal and drawing the penalty that led to New York's second goal.^[5] Richards concluded his 2010 campaign scoring five goals in his last seven matches helping New York to capture the Eastern Conference regular season title.^[6] In 2011, Richards enjoyed his most productive season to date, netting seven goals and providing seven assists in 27 matches.

Vancouver Whitecaps FC

Richards was traded to Vancouver Whitecaps FC on 13 July 2012 for Sébastien Le Toux and allocation money.^[7] At the time of the trade Richards stood second on New York's MLS league career list for games played, games started, and minutes played while placing third in assists.^[8] He scored his first goal for Vancouver against the San Jose Earthquakes on 20 July to put the Whitecaps up 1-0.

Burnley

On 26 August 2012 it was confirmed that Richards would join English Championship side Burnley on 1 January 2013 after the end of the MLS season and in the European transfer window.^[9] After initially appearing as a substitute in an FA Cup game,^[10] Richards appeared to struggle with his positioning on the field. He was given a second chance, this time in a Championship league game against Huddersfield, coming on after 15 minutes for the injured Dean Marney. Richards again struggled to acclimatise to the pace of the game, and was himself substituted after an hour.^[11] This would be his last appearance in a Burnley shirt, and he was sent out on loan shortly after.

Upon his return from his loan spell, Richards was released from his Burnley contract so that he could permanently join Norwegian side FK Bodø/Glimt.^[12]

Bodø/Glimt

After struggling to earn a starting place with Burnley, Richards was sent on loan to Norwegian 1. divisjon club Bodø/Glimt on 4 April 2013.^[13] He played in 14 league games and scored 2 goals before his loan period ended, and he returned to his parent club. In July 2013 Richards signed a permanent contract to finish out the season.^[12] He helped the club in capturing the 2013 Adeccoligaen and gain promotion to the top flight. On 13 April 2014 Richards helped Bodø/Glimt record their first victory of the Tippeligaen season, scoring the equalizer in a 4-2 come from behind win over Sogndal.^[14] He made a total of 55 official appearances for Bodø/Glimt, scoring ten goals.

Return to New York Red Bulls

On 7 March 2015 it was announced that Richards would be rejoining New York Red Bulls after spending the preseason as a trialist with the club.^[15] It was reported on 30 November 2015, that the Red Bulls would not be picking up Richards' option, ending his second stint with the club.^[16]

Indy Eleven

On 10 July 2015, the Red Bulls announced that Richards would be loaned out to NASL side Indy Eleven for the remainder of the season.^[17]

Miami FC

On 10 December 2015, it was announced that Richards had become the first ever signing for new North American Soccer League side Miami FC.^[18] He was released by Miami in December 2016.^[19]