Born in Brampton, Ontario, Hoilett was part of the Blackburn Rovers academy set up since the age of 13. He was initially unable to obtain a work permit while in England, and as a result, Blackburn loaned him to German clubs to help the player earn one in the future.
Hoilett made his debut for SC Paderborn (on loan) against Kickers Offenbach, coming on as a substitute for Sven Lintjens in a 3–2 victory on 3 February 2008, aged 17. Hoilett's first match in the starting eleven was against 1899 Hoffenheim on 9 March 2008.
Hoilett scored his only goal of his loan campaign on 18 May 2008 against Borussia Mönchengladbach in what would be his final game for the club.
Paderborn were later relegated, ending the 2007–08 2. Bundesliga season in 17th position.
Hoilett was loaned to another German club in the 2. Bundesliga, FC St. Pauli, for the 2008–09 2. Bundesliga season. He made his debut for the Hamburg-based side against SpVgg Greuther Fürth on 22 August 2008. He scored six times during his loan campaign with braces against Alemannia Aachen and Hansa Rostock, as well as individual goals against 1860 München and 1. FC Kaiserslautern. His final game would come in the form of a 1–0 loss against Rot Weiss Ahlen on 3 May 2009. St. Pauli finished the season in eighth position.
In January 2009, Hoilett's home club Blackburn applied for him to receive a work permit for him to play football in England. In the summer of 2009, Hoilett was granted a work permit on appeal, allowing him to continue his fledgling career in England at the Premier League level with Blackburn.
He scored his first and second goals for Blackburn since his full-time return to the club in only his third game, in a pre-season friendly against non-League club Leigh Genesis. He also earned Rovers a penalty in that game. His first competitive goal for Rovers came in a 3–1 League Cup win at Gillingham on 25 August 2009.
Hoilett was involved in Blackburn's dramatic League Cup win against Chelsea on 2 December 2009. Coming on as a second half substitution, he won an extra-time penalty which Benni McCarthy converted to put Rovers 3–2 up, but then missed a golden chance late on to seal victory before Paulo Ferreira equalised in the 122nd minute. However, Hoilett converted the crucial fifth penalty to help Rovers to the 4–3 shootout win and a place in the semi-finals. He then started his first league match on 12 December 2009 against Hull City, playing the full 90 minutes in a 0–0 draw at the KC Stadium. On 25 February 2010, with his contract due to expire in June 2010, Hoilett ended media speculation regarding his future at the club, by signing a new two-and-a-half year deal with Blackburn, keeping him at the club until the summer of 2012. On 9 May, he scored a header in a win over Aston Villa at Villa Park on the final day of the season, although the goal was later recorded as a Richard Dunne own goal. Hoilett made his first Premier League appearance of the 2010–11 season on 21 August 2010 by coming on for Nikola Kalinić in the 84th minute in a 2–1 defeat at St Andrew's against Birmingham City.
He scored his first goal of the 2010–11 season in the 1–0 victory over Queens Park Rangers in the FA Cup third round.
Hoilett scored his first league goal on 23 January 2011 in a 2–0 home victory against West Bromwich Albion at Ewood Park, converting in the 47th minute from a Nikola Kalinić assist. On 12 February 2011, he made his 40th Premier League appearance for Blackburn when he featured against Newcastle United at Ewood Park in a goalless draw, and was replaced at half-time due to a slight hamstring strain by Morten Gamst Pedersen. On 5 March, he scored his third goal of the season in a 3–2 defeat against Fulham in the 65th minute, away at Craven Cottage. He replaced by debutant Rubén Rochina on 82 minutes. His next goal came in the following game, a last gasp equaliser coming from a header against Blackpool at Ewood Park in a 2–2 draw. On 9 April 2011, he scored in the 1–1 draw versus Birmingham City at Ewood Park on half-time, but he unfortunately got injured in the 68th minute, being replaced by Australian Brett Emerton.
He scored his fifth league goal of the season with an individual goal, in a 3–2 win against Wolverhampton Wanderers at Molineux Stadium on the last day of the season. On 11 September 2011, in a game between Blackburn and Fulham, he was involved in a collision with Mark Schwarzer which resulted a head injury for Hoilett. He was eventually stretched off and Schwarzer received a yellow card. Hoilett scored a controversial second's goal in a match as Blackburn drew with Wigan Athletic 3–3 after teammate Morten Gamst Pedersen seemed to dribble the ball straight from a corner before firing in a low cross for Hoilett to head home from two yards.
In January 2012, Hoilett was named one of the 13 players to watch in 2012 by world football governing body FIFA.
In the 2011–12 season, Hoilett had the most dribbles per game among all Premier League players.
After refusing a contract renewal with Blackburn Rovers, Hoilett joined Queens Park Rangers on 27 July 2012 for a fee decided by tribunal. He signed a four-year contract. He scored his first goal for QPR in a 3–2 League Cup defeat to Reading on 26 September 2012. On 2 March 2013, Hoilett set-up teammate Loïc Rémy and played a crucial part in a 2–1 win over Southampton. A combination of injuries and poor form meant that Hoilett had a frustrating first season at QPR, which resulted in relegation to the Football League Championship.
Hoilett scored his first goal of the 2013–14 Football League Championship season in a 1–1 draw with Huddersfield Town. Four months later, he scored his second goal of the season in a comfortable 3–0 win over AFC Bournemouth at Loftus Road. Hoilett grabbed an assist for the only goal of the game, when he crossed for Bobby Zamora to score in the 89th minute in QPR's 1–0 victory over Derby County at Wembley Stadium in the 2014 Football League Championship play-off Final to gain promotion back to the Premier League after an absence of one season. After failing to agree a new contract with QPR at the end of the 2016–17 season, Hoilett left the club following the expiry of his contract.
Following the appointment of Neil Warnock as manager, Hoilett signed with Cardiff City on 6 October 2016, becoming Warnock's first signing at the club. His debut came on 14 October, against severnside rivals, Bristol City. Hoilett scored his first goal for Cardiff during a 3–2 victory over Huddersfield Town on 19 November 2016. He went on to score one more goal before signing a one-year contract extension in May 2017.
Hoilett's 2017–18 seasons account opened on 12 August, scoring in a 3–0 win over Aston Villa.
Hoilett was born in Brampton, Ontario. As a child, he captained Canada's representative team at the 2001 Danone Nations Cup in Paris.
Hoilett was eligible to play for Canada or Jamaica at international level. In February 2011, he rejected a call-up from the Canadian national team, stating that he wanted more time to develop his club career before committing to international football. In January 2012, Jamaica Football Federation president Horace Burrell confirmed that he had approached the player's father about Hoilett representing Jamaica.
In March 2012, Hoilett told various media bodies that he would consider playing for England if eligible. As Hoilett, his parents and grandparents were not born on the territory of The Football Association (FA), Hoilett needed to meet additional criteria established between the associations of the Home Nations. The Home Nations do not offer eligibility to play for their national teams based solely on a residency requirement; instead, they require players to be educated in the relevant FA's territory for five years before the age of 18. While Hoilett joined Blackburn at 13 years of age and did spend five years under contract to the club before turning 18, his two years spent living in Germany on loan to SC Paderborn and FC St. Pauli mean that he is not eligible for the English national team under the terms of the "Home nations agreement", which prevents players becoming eligible through residency and by requiring a foreign-national to undergo five years of education before the age of 18 in the territory of the Football Association he wishes to play for.
Hoilett officially declared for Canada in September 2015, prior to the fourth round of CONCACAF 2018 World Cup Qualifying. He received his first international cap in a 1–1 draw against Ghana on 13 October 2015 at RFK Stadium in Washington, D.C. He officially got cap-tied to Canada after starting for Canada in a 2018 World Cup Qualification match against Honduras. Hoilett was named to Canada's squad for the 2017 CONCACAF Gold Cup on June 27, 2017. His first goal for Canada came in the tournament quarterfinal, netting the lone Canadian goal in a 2-1 defeat to eventual Gold Cup finalists Jamaica on July 20.
Hoilett's father hails from Ocho Rios in Jamaica. Hoilett's brother is Canada U-20 international Jaineil Hoilett. who represented Canada at the 2009 CONCACAF U-17 Championship and Canada's U-20 team against the United States in December 2010.As of match played 16 September 2017
As of September 3, 2017
Scores and results list Canada's goal tally first.
Queens Park RangersFootball League Championship play-offs: 2013–14