BDO
Painter began playing darts around the age of 17 and represented Essex at county level. He made his televised World Championship debut at the 1994 BDO World Darts Championship, losing 3–2 to Kevin Kenny in the first round. He reached the second round the following year, where he lost to Martin Adams, but enjoyed success elsewhere in 1995 by winning the inaugural England Open. He added the British Open title in 1997.
Painter reached his first BDO World Championship quarter-final in 2000, losing 5–2 to eventual champion Ted Hankey. He also won the Swedish Open that year and made his debut in a PDC event at the 2000 World Grand Prix, reaching the second round before losing 3–2 to Phil Taylor. Despite this appearance, he initially remained a BDO player.
At the 2001 BDO World Darts Championship, Painter again reached the quarter-finals, losing 5–2 to Andy Fordham. He also made the quarter-finals of the World Masters and the Zuiderduin Masters that year. His growing involvement with the PDC included a notable victory over Taylor in the first round of the 2001 World Grand Prix, ending Taylor's unbeaten record in the tournament. Painter progressed to the quarter-finals before losing to Dennis Smith. He subsequently moved to the PDC circuit.
PDC
2002–2005: World Championship runner-up
Painter made his PDC World Championship debut at the 2002 tournament, losing in the first round to Ronnie Baxter. His results improved significantly at the 2003 World Championship, where he reached the semi-finals before losing 6–4 to eventual champion John Part.
His most notable World Championship performance came in 2004. Seeded tenth, Painter defeated Paul Williams, Ronnie Baxter, Mark Dudbridge and former world champion Bob Anderson to reach his first world final. Facing Taylor, he established a 4–1 lead in sets before his opponent fought back. The match eventually reached 6–6 in sets and 5–5 in legs in the deciding set, requiring a sudden-death leg. Taylor won the final leg to secure a 7–6 victory, while Painter finished as runner-up after coming close to winning his first world title.
Painter continued to perform well in 2004, reaching the quarter-finals of the UK Open and semi-finals of the Las Vegas Desert Classic. At the 2005 World Championship, he reached the quarter-finals but was defeated 5–1 by Taylor. He also made the quarter-finals of the 2005 Las Vegas Desert Classic. However, a leg injury disrupted his schedule and affected his form.
2006–2010: Decline and resurgence
Painter reached another World Championship quarter-final in 2006, again losing to Taylor, and won a UK Open regional qualifying event. However, his results deteriorated during the year and he dropped out of the world's top 16. At the 2007 PDC World Darts Championship, he suffered a first-round defeat to former practice partner Colin Osborne.
His form improved towards the end of 2007. He reached the quarter-finals of the inaugural Grand Slam of Darts and enjoyed a successful run at the 2008 PDC World Darts Championship. After defeating defending champion Raymond van Barneveld in the third round, Painter reached the semi-finals before losing 6–2 to eventual champion John Part.
Although his televised results were inconsistent during 2008, Painter remained competitive on the PDC Pro Tour. In 2009, he reached the semi-finals of the UK Open, defeating Dennis Priestley and Alan Tabern before losing 10–7 to Colin Osborne. He also made the quarter-finals of both the World Grand Prix and Grand Slam of Darts.
At the 2010 World Matchplay, Painter produced a comeback from 8–2 down to defeat Colin Lloyd 11–9 in the first round. He subsequently beat Mark Walsh 14–12 to reach his first World Matchplay quarter-final. His run ended with a 16–4 defeat to Phil Taylor.
2011–2014: First PDC major title
After a disappointing start to 2011, including a first-round exit from the World Championship, Painter achieved the biggest success of his PDC career at the Players Championship Finals in December. He defeated Colin Osborne, Gary Anderson and Mervyn King before recovering from 9–6 down to beat Scott Rand 10–9 in the semi-finals. Painter then defeated Mark Webster 13–9 in the final to win his first televised PDC major title and collect £60,000 in prize money. The victory lifted him into the world's top ten.
His major victory earned him a wildcard invitation to the 2012 Premier League, his only appearance in the competition. Despite recording victories over Gary Anderson, Simon Whitlock, Andy Hamilton and Adrian Lewis, he finished seventh out of eight players. Later in 2012, Painter reached the quarter-finals of the Grand Slam of Darts, losing 16–12 to Dean Winstanley. He was unable to defend his Players Championship Finals title, losing to Michael van Gerwen in the first round.
In 2013, Painter reached the third round of the World Championship, where he lost to Adrian Lewis. He also made the last 16 of the European Championship, World Matchplay and World Grand Prix. His most notable performance of the season came at Players Championship 12, where he reached his first PDC ranking final since his 2011 major victory, but was whitewashed 6–0 by Kim Huybrechts.
Painter reached the third round of the 2014 World Championship, losing 4–0 to Simon Whitlock. He subsequently enjoyed two major quarter-final appearances, at the UK Open and World Grand Prix. At the latter event, he recovered from two sets down to defeat Adrian Lewis 3–2 in the second round, before losing by the same scoreline to Gary Anderson in the quarter-finals.
2015–2018: Final years on the PDC Pro Tour
Painter's results declined during the following seasons. At the 2015 World Championship, he established a 3–1 lead against Spanish qualifier Cristo Reyes in the second round, but lost 4–3. He failed to qualify for the World Matchplay for the first time since joining the PDC and missed the remaining major tournaments that year, although he retained a place in the world's top 32.
At the 2016 World Championship, Painter defeated Kim Viljanen before losing 4–1 to Phil Taylor in the second round. He continued to fall down the PDC Order of Merit, dropping outside the top 32 during the year.
Painter qualified for the 2017 World Championship following the withdrawal of Kyle Anderson. He defeated Jamie Caven 3–1 in the first round but again lost to Taylor, this time 4–0 in the second round. Despite his declining ranking, Painter reached the final of Players Championship 17 in August 2017, his first PDC ranking final for almost four years. He defeated Gerwyn Price and Jermaine Wattimena in the closing rounds before losing 6–2 to Kyle Anderson in the final.
Painter made his final appearance at the PDC World Championship in 2018, losing 3–0 to Mensur Suljović in the first round. He subsequently struggled to qualify for major tournaments and lost his PDC Tour Card at the end of the 2018 season, ending his long spell as a regular participant on the professional circuit.
2019–2021: Challenge Tour and retirement from professional darts
Painter attempted to regain his Tour Card at the 2019 PDC Qualifying School. On the final day, he reached the semi-finals after defeating Gavin Carlin 5–4 in the quarter-finals, but lost 5–2 to Kirk Shepherd. The defeat prevented him from securing an immediate return to the Pro Tour.
Without a Tour Card, Painter competed on the PDC Challenge Tour in 2019 and 2020. His best result during this period was a quarter-final appearance at the fifth Challenge Tour event of 2020, where he lost to Maikel Verberk.
Painter returned to Q-School in 2021 and advanced to the final stage, but again failed to regain a Tour Card. On 17 February 2021, he announced his retirement from professional darts after approximately 25 years at the highest level. Painter explained that he no longer wished to continue the demands of Q-School and the Challenge Tour, although he remained open to exhibitions and other forms of competitive darts.
World Seniors Darts Tour and later career (2022–present)
Painter returned to televised competition at the inaugural 2022 World Seniors Darts Championship. He defeated Tony O'Shea and Wayne Warren before recording a 3–0 quarter-final victory over his long-time rival Phil Taylor. However, he lost 4–2 to eventual champion Robert Thornton in the semi-finals.
Later in 2022, he suffered a 4–3 preliminary-round defeat to David Cameron at the World Seniors Masters. At the inaugural World Seniors Matchplay, Painter again reached the semi-finals. He defeated Colin McGarry 8–5 in the quarter-finals before losing 12–10 to Phil Taylor, having missed opportunities to win the match.
Painter repeated his World Seniors Championship semi-final appearance in 2023. He defeated Ronnie Baxter, Dennis Harbour and Mark Dudbridge, but was once again eliminated by Robert Thornton, losing 3–0 in the semi-finals.
He also reached the quarter-finals of the inaugural World Seniors Champion of Champions, losing 10–5 to David Cameron. At the 2023 World Seniors Masters, he was defeated 4–3 by John Part in the first round. Later that year, Painter progressed to the quarter-finals of the World Seniors Matchplay, where he lost 9–7 to Jim McEwan.
At the 2024 World Seniors Championship, Painter recovered from two sets down to defeat Jim McEwan 3–2 in the opening round before losing 3–1 to eventual champion John Henderson in the second round. He also competed in the 2024 World Seniors Matchplay, where he was defeated 8–3 by David Cameron in the first round.
Painter suffered another early exit at the 2025 World Seniors Darts Championship, losing 3–2 to Richie Burnett in the first round after having led by two sets. He also participated in the 2025 World Seniors Champion of Champions, losing 5–2 to Mervyn King in the opening round.
Despite his earlier retirement from the professional circuit, Painter continued playing competitive darts. In 2026, he entered the PDC Qualifying School, explaining that his primary intention was to gain match practice and qualify to play on the Challenge Tour rather than to pursue another Tour Card. In an interview published in February 2026, he discussed a prolonged struggle with dartitis, which he associated with anxiety and stress, and said that changes to his throwing routine had helped him make significant progress.
Painter competed in several Challenge Tour events during 2026, reaching the last 32 at Event 16 in Milton Keynes in August. He also appeared in the MODUS Super Series during the year, continuing to participate in competitive darts outside the main PDC Pro Tour.
