Born in England, he won seven caps for Jamaica in 2013. He began his career at Watford, making his debut in the English Football League in April 2006 and his debut in the Premier League in May 2007. He was loaned out to Southern League side Wealdstone in 2007, and then League Two side Hereford United, and scored 16 goals in 52 appearances to help Hereford win promotion in the 2007–08 season. He spent the 2008–09 season on loan at Southend United and was sold on to Huddersfield Town in July 2009. He was loaned out to Millwall in September 2010 and joined the club permanently in January 2011. The following month, he was loaned out to Derby County and joined the club permanently in the summer. He rejoined Huddersfield Town on loan in February 2013 and was sold to Doncaster Rovers in August 2013. He joined Scunthorpe United on loan in March 2015.
In August 2007, Robinson joined League Two side Hereford United on a four-month loan, alongside teammate Toumani Diagouraga.[7] He scored his first goal in the Football League on 18 August, in a 2–1 win at Barnet.[8]ManagerGraham Turner compared him to a young Steve Bull,[9] saying that "he's very lively, he's got pace, and gets himself into good positions."[10] Robinson finished the season as top goalscorer for Hereford with 16 goals in all competitions as they achieved promotion in third-place. With Darius Henderson suspended, Watford manager Aidy Boothroyd was hoping to use Robinson in the Championshipplay-offs, but confirmed that he was unable to do so due to the terms of Robinson's loan deal at Hereford.[11]
Robinson made four appearances for Watford in the 2008–09 season, but was not in new manager Brendan Rodgers's first-team plan's, who replaced Boothroyd as manager in November.[12] On 24 January 2009, Robinson joined League One side Southend United on loan until the end of the 2008–09 season. He formed an effective strike partnership with Lee Barnard and impressed manager Steve Tilson with his performances.[13] Tilson made a bid for Robinson at the end of the season.[14] Though Rodgers left Watford and was succeeded by Malky Mackay, Robinson had already decided to leave the club.[15]
Huddersfield Town
In July 2009, Robinson signed for League One club Huddersfield Town on a three-year deal for an undisclosed fee.[16] He chose Huddersfield ahead of several other clubs, including Swindon Town, who had a "verbal agreement" to sign Robinson from Watford for £275,000 according to manager Danny Wilson.[17] Swindon chairman Andrew Fitton stated that "We agreed a deal with the club and player but there are shenanigans going on that we have warned certain people about. This is a classic example of agents and greed."[18] On 26 August, he scored two goals in a 4–3 League Cup defeat to Newcastle United at St James' Park.[19] He began the season in a strike partnership with Jordan Rhodes before being dropped fin favour of Lee Novak.[20] He ended the 2009–10 season with 16 goals in 43 appearances.
He was linked with a move away from Huddersfield in June 2010, but manager Lee Clark said that the rumours did not come from the Galpharm Stadium and that "it seems as though someone is trying to orchestrate a move."[21]
Millwall
On 8 September 2010, after falling down the pecking order at Huddersfield, Robinson moved to Millwall on a 93-day emergency loan.[22] He returned to Huddersfield in early November through injury, with the need for an operation on his knee, cutting his loan spell short. He joined Millwall on a two-and-a-half-year deal for an undisclosed fee in January 2011.[23] Manager Kenny Jackett said that Robinson would want to prove Huddersfield wrong, and therefore have a hunger to perform at The Den.[24]
Derby County
In February 2011, Robinson signed a three-month loan deal at Championship club Derby County, with a view to a permanent move.[25] Robinson scored twice in 13 games during this loan spell. He impressed manager Nigel Clough, who told BBC Radio Derby that "hopefully Theo will be here next season as well, as one of five or six strikers."[26] He joined Derby on a two-year contract after his contract with Millwall ended in the summer.[27]
Despite being Derby's second top-scorer with three goals in six league starts, Robinson was sometimes criticised by supporters on Twitter for not scoring enough goals and being "rubbish".[28] He answered his critics by scoring a brace in Derby's 3–2 defeat at Peterborough United, taking his tally for the season up to six, making him the club's top-scorer.[29] Robinson finished the 2011–12 season with 12 goals in all competitions and joint top-scorer with Steve Davies.
The club reprimanded Robinson after he broke club rules by posting on Twitter that he was dropped from the matchday squad before the team was announced for the game at Bolton Wanderers on 21 August 2012.[30] Four days later, Robinson came off the bench to score a last-minute equaliser against Wolverhampton Wanderers.[31] He struggled to get into the starting line-up as Conor Sammon and Jamie Ward were Clough's preferred attackers. Still, Robinson regained his place in the starting line-up after an injury to Ward, and Clough praised Robinson for his improved work ethic, saying, "... he's doing his job now... he now has seven goals for the season and he is liable to get goals."[32] On 22 February 2013, after asking to leave on loan to get regular first-team football, Robinson rejoined his former club Huddersfield Town on an emergency loan to the end of the 2012–13 season.[33] Upon his return to Pride Park in May, Robinson was made available for transfer with one year left on his contract.[34]
Doncaster Rovers
In August 2013, Robinson signed with Doncaster Rovers on a two-year contract for an undisclosed fee.[35][36] The fee was undisclosed but was reported to be in the region of £150,000.[37] He scored his first goal for the club on his debut the following day, in a 2–0 win over Blackburn Rovers.[38] He ended the 2013–14 campaign with five goals in 31 Championship games as "Donny" were relegated into League One.
Robinson signed for Scottish Premiership side Motherwell in August 2015 on a contract running until the end of the 2015–16 season.[42] He said that he was attracted to the club as he was already friends with teammates Lionel Ainsworth and Stephen Pearson.[43] He was initially used as a substitute by manager Ian Baraclough.[44] He fell out of the first-team picture under new manager Mark McGhee, who later said that "It's not quite worked out for Theo here at Fir Park, but that can happen, particularly if the manager who signs you leaves so soon after you arrive."[45]
Port Vale
In January 2016, Robinson signed for League One side Port Vale on a contract running until the end of the 2015–16 season.[46] He was initially used as a substitute at Vale Park, but began starting games as he claimed to be "getting fitter, stronger and sharper with each game".[47] He scored his first goal for the club on his eighth appearance, the opening goal of a 2–0 home win over Colchester United on 5 March.[48] He was released upon the expiry of his contract at the end of the season.[49]
Lincoln City
Robinson signed a short-term contract with National League club Lincoln City in October 2016.[50] On 7 January, he scored both of the "Imps" goals in a 2–2 draw with Championship side Ipswich Town in an FA Cup third round tie at Portman Road.[51] He also scored against Brighton & Hove Albion in the following round, and left Lincoln with the club in the fifth round of the FA Cup and top of the National League.[52]
Southend United
Robinson returned to EFL League One when he joined Southend United for an undisclosed fee on a two-and-a-half-year contract on 31 January 2017.[52] Manager Phil Brown had rejected the chance to sign Robinson the previous summer after the player had a trial at the club, and admitted he had made a mistake in doing so.[53] He made 18 appearances in the second half of the 2016–17 season and signed a one-year contract extension in August 2017.[54] However, he made just two league starts in the first half of the 2017–18 season and rejected the chance to join Colchester United on loan in January after his preferred option of Lincoln City were rebuffed by chairman Ron Martin.[55] He was instead restored to the first-team at Roots Hall by new manager Chris Powell, and scored a hat-trick in a 4–0 win over Milton Keynes Dons on 21 April to earn himself a place on the EFL team of the week.[56] He was nominated for that month's PFA Fan's Player Of The Month award.[57][58]
Robinson began the 2018–19 season on the bench, though did score three goals in his five starts by the start of October.[59] He went on to make 13 league starts and 11 substitute appearances in the first half of the campaign, scoring four goals.[60] On 31 January, he joined EFL League Two side Swindon Town on loan until the end of the 2018–19 season.[61] He went on to score seven goals in 16 games for the "Robins", helping to relegate Notts County with a brace at the County Ground on the final day of the season.[62] Swindon manager Richie Wellens was reportedly keen to sign him permanently once the loan spell came to an end.[63]
On 29 August 2019, Robinson joined League Two side Colchester United on loan until January 2020.[64] He scored his first goal for "U's" in their 3–2 EFL Trophy win against Gillingham on 3 September.[65] After a relatively successful start to the campaign for Robinson, the loan deal was extended until the end of the 2019–20 season on 14 January.[66] On 11 February, he scored his 100th Football League goal in a 3–2 defeat at Grimsby Town.[67] He had scored 12 goals in 36 games by the time the 2019–20 season was ended early in March due to the COVID-19 pandemic in England; Southend would be relegated after the table was concluded on a points per game basis.[68][69] He returned to Colchester to play in the play-off semi-finals, which ended in a 3–2 aggregate defeat to Exeter City.[70][71] He scored at a rate of one every 157 minutes during his loan spell, a statistic bettered only by Eoin Doyle in League Two.[72] He confirmed his departure from Southend in June 2020.[73]
Return to Port Vale
On 24 August 2020, Robinson rejoined Port Vale on a two-year deal, where he faced competition from Tom Pope, Mark Cullen and Devante Rodney for a place in the starting eleven.[74] He stated that "when I was here before it wasn't really a good time personally but now I am here to put things right".[75] It was reported that Grimsby manager Ian Holloway had tried to sign him but lost out due to his club insisting on a clause to reduce pay if the league was postponed or cancelled again due to a second wave of Coronavirus disease 2019 cases; Vale reportedly had no such clause in their contract offer.[76] On 5 September, he scored on his second debut for the Vale, coming on as a substitute to score a late winner in a 2–1 victory over Scunthorpe United in the first round of the EFL Cup, manager John Askey said that "It's nice when you have someone like Theo who can come on and has goals in him".[77] Robinson set a personal target of 10 goals for the campaign but said the main aim was promotion.[78] Having started the 2020–21 season on the bench, he claimed a place in the starting eleven by mid-October after becoming the club's leading scorer.[79] He soon dropped out of the starting eleven however, and was transfer-listed in December.[80]Caretaker managerDanny Pugh deregistered Robinson from the club's 22-man squad the following month in order to make room for new signing Kurtis Guthrie.[81] He was re-registered at the end of the January transfer window and went on to earn praise for his work rate from new manager Darrell Clarke but was still transfer-listed in May 2021.[82][83][84] He left the club by mutual consent on 31 August 2021.[85]
Bradford City
Having secured his release from Port Vale, Robinson signed a one-year contract with League Two club Bradford City after manager Derek Adams needed cover for the injured Lee Angol.[86] He was dropped by new manager Mark Hughes in early March. He did not feature again at Valley Parade, leaving his final tally at four goals in 26 appearances, of which only five appearances were league starts.[87][88] Robinson was released at the end of his one-year deal.[89] Robinson was a trialist for Mansfield Town in August 2022 but was not offered a contract.[90]
Hartlepool United
On 13 October 2022, Robinson had signed for League Two side Hartlepool United.[91]Interim managerKeith Curle said that "Theo is a player we've tried signing before and he's turned down other offers to join".[92] Robinson left the club on 26 November 2022, with Curle stating that: "Theo is no longer with us. It was my choice."[93]
Later career
In March 2023, Robinson signed for National League North club Brackley Town.[94][95] He started eight games and made six substitute appearances in the remainder of the 2022–23 season as Brackley reached the final of the play-offs, where they were beaten 2–0 by Kidderminster Harriers.[60][95] In January 2024, Robinson signed for Gloucester City in the National League North on a contract until the end of the 2023–24 season.[96] Despite scoring seven goals in 17 games, Gloucester were relegated in 23rd place.[60]
In August 2024, Robinson joined Southern Premier Division Central club Bromsgrove Sporting.[97]