Pipe was a boxer in his youth and as a staunch anti-smoker he refused to play darts in local pubs as the cigarette smoke would make his eyes water. In 2007, a smoking ban was introduced to England which enabled him to restart his darts career. He first emerged at the 2008 UK Open as a pub qualifier. He defeated Geoff Wylie and Lionel Sams before losing 9–3 to James Wade in the third round. Following this performance, he joined the PDC Pro Tour and reached the same stage of the UK Open a year later, this time losing 9–5 against Andy Jenkins.

He qualified for the 2010 Grand Slam of Darts as one of four ITV Wildcard qualifiers. He lost all three of his group games to James Wade, Vincent van der Voort, and Tony O'Shea.

Pipe also qualified for the 2011 PDC World Darts Championship, losing 1-3 in the first round to Mark Walsh. In June 2011, Pipe hit a nine-dart finish in a Players Championship match in Nuland against Colin Osborne. Pipe made his World Matchplay debut in 2011. He defeated Mervyn King 10-6 in the first round. In October, Pipe won his first PDC Pro Tour event in Dublin, defeating Phil Taylor 6-5 in the final. On 5 November, Pipe won his third Players Championship in just a month.

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