Roofe started his career with West Bromwich Albion where he played for the side’s academy team, while attending Joseph Leckie Community Technology College in Walsall. In July 2009, Roofe was among eleven academy youngsters to sign scholarships with West Brom. In April 2011, he was sent out on loan to Icelandic side Víkingur Reykjavík, where he made three appearances, scoring one goal in the Icelandic Cup. In January 2012, Roofe signed his first professional contract, on an 18-month deal with an option to extend.

On 27 September 2012, he joined Football League Two side Northampton Town on a one-month loan deal. He made his professional debut on 29 September 2012, in a 3–3 draw with Burton Albion, coming on as a substitute for Chris Hackett. After making six appearances for the club, it announced that Roofe would return to his parent club on 27 October 2012. Following the end of the 2012–13 season, Roofe’s contract with West Brom was extended for one year.

In the 2013–14 season, Roofe joined Football League Two side Cheltenham Town on loan until 4 January 2014. He made his debut for the club, two days after joining, in a 1–1 draw against Southend United. Roofe scored his first goal for the club in a 2–2 draw against Hartlepool United on 14 December 2013. On 9 January 2014, Roofe’s loan spell with Cheltenham Town was extended for another month. After making nine appearances, Roofe informed the club that he wanted to return to his parent club. However, on his return, Roofe returned to the club’s reserves throughout the 2013–14 season. Nevertheless, his contract with the club was extended further by twelve months.

In the 2014–15 season, Roofe scored in a friendly match against Port Vale, which West Brom lost. Then, on 4 November 2014, he joined Football League One side Colchester United on a month’s loan. A week later, Roofe made his debut for the club, where he came on as a substitute for Sanchez Watt in the second half, in a 3–2 loss against Barnsley. After making two appearances, Roofe’s loan spell with Colchester United came to an end and he returned to West Brom.

On 13 February 2015, Roofe joined Oxford United on loan from West Bromwich Albion. Roofe made his Oxford United debut the next day, coming on as a substitute for Andy Whing in the 61st minute, in a 2–0 defeat to Burton Albion. Despite his not scoring in his first five appearances, Roofe’s loan spell with Oxford was extended until the end of the season. Roofe then scored his first Oxford United goals, in a 3–2 win over Wycombe Wanderers on 3 April 2015, and he added four further goals in the last three matches against Tranmere Rovers, Cambridge United and Newport County. His final goal tally for the season was six goals in sixteen appearances.

Weeks after the 2014–15 season ended, Roofe signed a three-year permanent deal with the club on 11 May, for an undisclosed sum. On 11 August 2015, he scored from 40 yards in a 0–4 League Cup upset of Championship side Brentford.

On 10 January 2016, Roofe scored twice for Oxford in a 3–2 victory to knock Premier League side Swansea City out of the FA Cup. On 15 March 2016, Roofe scored his first hat-trick in the 4–0 win against Dagenham & Redbridge. Roofe’s 4 goals in the Football League Trophy, including 2 against rivals Swindon Town, were instrumental in Oxford reaching the 2016 Football League Trophy Final at Wembley Stadium against Barnsley on 3 April 2016; his cross allowed Danny Hylton to score in the second half, but Barnsley held on for a 3–2 win.

In April 2016 he was voted Football League Two’s Player of the Year at the Football League Awards and was also named in the League Two PFA Team Of The Year. He scored 26 goals in 49 appearances in all competitions during the 2015–16 season for Oxford, in which they finished second in League Two and gained promotion to League One.

On 7 July 2016, Roofe signed for Championship side Leeds United on a four-year deal for an undisclosed seven-figure fee. On 5 August, Roofe was given the squad number 7 shirt for the 2016–17 season. On 7 August, Roofe made his Leeds debut against Queens Park Rangers in a 3–0 defeat. Roofe was initially credited with his first goal for Leeds in a 1–0 win at Wolverhampton Wanderers on 22 October, however it was later adjudicated to be an own goal by Wolves defender Sílvio. After starting the season predominantly on the left side of midfield, after an injury to playmaker Pablo Hernández on 5 November against Norwich City, Roofe found himself playing in an attacking midfield role.

On 29 November 2016, Roofe came close to scoring his first Leeds goal when he saw his long range shot smash off the inside of the post after beating goalkeeper Simon Mignolet, in EFL Cup quarter-final match against Liverpool at Anfield in a 2–0 defeat, after the match Roofe jokingly Tweeted about being under a goalscoring curse with the Hashtag #Pray4Roofe. However, Roofe quickly ended the drought in the following game when he scored his first goal for Leeds United against Aston Villa in a 2–0 victory on 3 December 2016. On 26 December 2016, Roofe scored his second goal for Leeds in a 4–1 victory against Preston North End; he also provided two assists in the same game.

He scored his first goals of the 2017–18 season on 22 August 2017, scoring a hat-trick in Leeds’ 5–1 EFL Cup victory against Newport County, thus equalling his goal tally for the previous season for Leeds. On 26 August, Roofe starting up front in place of the departed Chris Wood, scored his first league goal of the season a 2–0 victory against Nottingham Forest. He scored a hat-trick on 10 December in Leeds’ 1–3 victory against Queens Park Rangers.

Roofe scored his 10th goal of the season in all competitions on 26 December in Leeds’ 1–2 victory against Burton Albion. After 6 weeks out with a calf injury, Roofe returned to Leeds’ starting lineup on 10 April 2017, and scored his 13th goal of the season in all competitions (his 10th in the League) in a 3–1 loss against Preston North End.

On 16 April 2018, Roofe was nominated as one of four players for Leeds United’s Player of The Year award. On 6 May 2018, Roofe scored his 14th goal of the season 2–0 home victory against Queens Park Rangers on the final day of the season. He finished the season as the club’s top scorer with 14 goals, ahead of Pierre-Michel Lasogga who had scored 10.

He was nominated for the EFL Championship Player of the Month award for December 2018, having scored five goals during the month (including three over four days, all in injury time), but lost out on the award to Hull City winger Jarrod Bowen. He scored his 14th goal of the season (which overtook his previous seasons tally of 13) in a 2–0 win against Derby County on 11 January 2019.

However, after playing through Leeds’ 2–1 victory against Swansea City on 13 February 2019, after being pictured wearing a leg brace, on 19 February it was announced by the club that Roofe had a knee ligament injury and would face a period out during Leeds’ race for promotion. Roofe returned as a substitute during 6 April away game to Birmingham and his appearances since then were limited to spells off the bench, with Bielsa favouring Patrick Bamford as the sole striker.

During the 2018–19 Leeds United F.C. season, Roofe played 34 games in all competitions, scoring 15 goals, after Leeds finished the regular season in third place after dropping out of the automatic promotion places with 3 games left after a defeat to 10 man Wigan Athletic on 19 April, Leeds qualified for the playoffs, Roofe started the first leg of the Championship play-offs at Pride Park on 11 May 2019, netting the sole goal of the game against sixth-placed Derby County for his 15th goal of the season. but was replaced by Patrick Bamford for the 2nd leg at Elland Road after picking up an injury in the 2nd half of the match during the 1–0 win at Pride Park. With Roofe out injured, Leeds lost 4–2 in an encounter that saw both teams reduced to 10 men and Derby progress to the final against Aston Villa, having won 4–3 on aggregate.

Roofe joined Anderlecht for an undisclosed fee on 6 August 2019. In his opening seven games in the Belgian league, Roofe scored five times, including an 81st-minute winner at Zulte Waregem. Anderlecht had a slow start to the season and by the end of October were in 10th position. In the last months of 2019, Roofe scored a number of goals, with five of them leading to Anderlecht winning or drawing over a six-week period. Losing only one of seven league games during this period, Anderlecht remained in 10th place in the league.

In June 2019, Roofe received an invitation to play for the Jamaica national side for the CONCACAF Gold Cup in July 2019.

In August 2019, Roofe was one of the main stars of Leeds United documentary ‘Take Us Home’, documenting the 2018–19 season on Amazon Prime featuring in several episodes. The documentary was narrated by Academy Award winning actor and Leeds United fan Russell Crowe.

On 4 August 2020, Roofe signed for Rangers, on a four-year deal, for an undisclosed fee. The fee was believed to be €5 million.

On 22 October 2020, Roofe scored from his own half in stoppage time of the club’s 2-0 UEFA Europa League group stage away win at Standard Liège. Roofe’s shot was measured at 54.6 yards (49.9m) out – making it the longest-range goal ever scored in the history of the UEFA Cup/Europa League. This record was broken the following week by Omonia player Jordi Gómez.