Webster made progress once he was aged 12 and could play in Local Darts Leagues in public houses in his native North Wales.

Despite his lack of major television tournament wins, Webster entered the 2008 BDO World Championship as the number one seed due to his success in open events.

This time around, Webster justified his status as joint-favourite for the title (alongside Anderson), as he beat Ian Jones in the first round, popular qualifier Glenn Moody in the last 16 and ninth seed Darryl Fitton in the quarter-finals.

Having beaten Martin Atkins, he lost to wildcard entrant Henny van der Ster who claimed the quarter final spot ahead of Webster and went on to reach the semi-finals.

In his debut at the PDC World Championship in 2010, Webster defeated established players including Mark Walsh, Peter Manley and Co Stompé to reach the semi-final, where he was outplayed by Taylor.

He began 2010 poorly with repeated early exits in Floor events but found form by a few quarter final appearances and by reaching consecutive semi-finals in a Players Championship and UK Open Qualifier 8 in Wigan during May.

After the UK Open his poor floor form returned in which he failed to progress past the last 32 in any event until the 2010 World Matchplay Darts in which he knocked out seventh seed Adrian Lewis 11–9 in the first round but was beaten 13–9 by Co Stompé This earned him £7,500 towards the order of merit.

After beating New Zealand in their first game 6–4 Webster and Bates became the surprise package of the tournament topping their group in the next stage which included wins over the Scottish pairing of Gary Anderson and Robert Thornton and the Spanish team of Carlos Rodriguez and Antonio Alcinas who had knocked out the England team consisting of world number one and two Phil Taylor and James Wade.

He continued this good form into the 2011 PDC World Darts Championship in which he knocked out Steve Maish, number 8 seed Ronnie Baxter and Mark Hylton in the early rounds losing only 1 set between them.

[citation needed] Webster reached his second quarter-final at the Grand Slam of Darts, once again beating John Part en route to a defeat by Lewis.

[citation needed] His good form from the previous week did not help him, however, at the 2012 World Championship where he was upset by fellow countryman, Richie Burnett, 2–3.

Webster had a dart at double top in the deciding set to win the match, but missed and was the highest seed to exit in the first round of the event.

[10] In September, Webster threw a nine darter in the opening leg of his first round match against Andree Welge in Event 4 of the European Tour, but went on to lose 4–6.

[14] He played in his third World Cup of Darts and second with Richie Burnett and they reached the semi-finals where they faced the number one seeds of Phil Taylor and Adrian Lewis.

[17] Webster beat Wes Newton 5–2 in his opening group game of the Grand Slam of Darts but then lost 5–1 against Simon Whitlock to need a win over Ross Smith to stand a chance of qualifying for the last 16 and he did so 5–3.

Webster had already scored enough to not require throwing his final three darts to eliminate Newton and was then defeated 10–6 by reigning BDO world champion Scott Waites.

[21] He stated after the van Barneveld match that coming into the event his career was on the line as he was close to dropping out of the top 32, but by earning £25,000 for reaching the last eight his place was secured.

[26] In November, Webster lost to Jay Foreman 4–2 in the Grand Slam of Darts Wild Card Qualifier which meant that he failed to play in the event for the first time.

[31] Webster played with Jamie Lewis at the World Cup for the first time and they suffered a surprise 5–3 loss to Hong Kong in the opening round.

[36] 5–3 wins over Keegan Brown and Michel van der Horst helped Webster qualify from his group at the Grand Slam and he then took out 10 of his 14 attempts at a double to eliminate Gary Anderson 10–6.

[40] He defeated Matthew Edgar 9–3, Dirk van Duijvenbode 9–4 and Mensur Suljović 9–5 to reach his third major quarter-final in six months and was comfortably beaten 10–3 by Phil Taylor.

[42] After his 10–6 defeat to Adrian Lewis in the opening round of the World Matchplay, Webster said that dartitis, which he has fought over the past few years, was evident in the latter half of the game and that he was trying to beat the player and himself during matches.