He began his career with Manchester City in the Premier League, before spending the remainder of his time in England with Southampton, Plymouth Argyle, Charlton Athletic and Brentford.

He is a two-time MLS Golden Boot winner and currently holds the New York Red Bulls record for most goals scored.

Internationally, Wright-Phillips earned five England U20 caps in 2005 and, after moving to North America, rejected the opportunity to represent Jamaica through his family background.

On 11 December 2010, Wright-Phillips scored both goals against Exeter City in the Devon derby in a 2–0 Plymouth win, the second marked his 12th of the season.

Of note, he scored the winner in a friendly against his father's former team Arsenal,[21] and the equaliser against Bayern Munich in the 2014 MLS All-Star Game.

Two days after the All-Star game, Red Bulls Sporting Director Andy Roxburgh claimed that Wright-Phillips' scoring exploits were producing international transfer interest in the player.

[26] He scored his third play-off goal against D.C. United in the first leg of the 2014 MLS Eastern Conference semi-final, helping New York to a 2–0 victory.

In the first leg Wright-Phillips recklessly encroached upon Revolution goalkeeper Bobby Shuttleworth on a throw, earning his second yellow of the playoffs.

[29] On 22 March 2015 Wright-Phillips scored his first goal of the season and assisted Lloyd Sam on another in a 2–0 victory over rival D.C. United at Red Bull Arena earning him MLS Player of the Week honors.

[31] On 10 May, he scored both goals as the Red Bulls won 2–1 at home against New York City FC in the first Hudson River derby between the two franchises,[32] and equalised in a 3–1 victory at the rivals' Yankee Stadium on 28 June.

[37] On 25 October Wright-Phillips scored the opening goal for New York in 2–1 victory over Chicago, helping Red Bulls clinch the 2015 MLS Supporters' Shield.

[38] In the second leg of the Conference semi-finals against D.C. United in the 2015 MLS Cup Playoffs, Wright-Phillips scored the only goal of the game in added time, and his team advanced 2–0 on aggregate.

[39] On 24 April 2016, Wright-Phillips scored his first two goals of the season in helping New York come from behind to win 3–2 over Orlando City SC.

[49] On 23 October, Wright-Phillips captured his second MLS Golden Boot title in three years, beating cross town rival, David Villa by one goal.

[50] On 22 February 2017, Wright-Phillips scored his first CONCACAF Champions League goal for the club in a 1–1 draw against Vancouver Whitecaps FC in the quarterfinals.

[53] One month later on 15 August, Wright-Phillips scored a brace against FC Cincinnati, including a goal in the 101st minute to send New York to their first Open Cup final since 2003.

On 6 March he scored two goals to lead New York to a 2–0 victory in Mexico over Club Tijuana in the CONCACAF Champions League.

[69] He further made his league debut for Columbus in a 0–0 draw against the Philadelphia Union, coming on as a substitute for Gyasi Zardes.

[71][72] On 9 March 2022, Wright-Phillips announced that he signed a one-day contract to retire as a New York Red Bull, following which he was appointed "Special Assistant to the Sporting Director".

[74] He was called up again that summer for the 2005 Toulon Tournament where he played Tunisia,[75] South Korea[76] and the third-place playoff penalty shootout victory over Mexico.

In 2014, he clashed fellow footballer Yannick Bolasie for the long running grime DVD series Lord of the Mics.