[6] Following these appearances, he signed a three-year contract with Hawke's Bay at the end of 2006,[7] and intended to start studying sport and recreation & business management at the Eastern Institute of Technology the following year.

[8] Selected out of the Taradale Rugby Club,[9] Guildford made his debut for Hawke's Bay in 2007 aged 18, making him one of the youngest players to play in the Air New Zealand Cup.

[15] With fellow wings Ben Smith, Julian Savea, Charles Piutau, Cory Jane, and Frank Halai being preferred by the All Blacks, Guildford sought an overseas contract.

[19] He was meant to join Clermont at the conclusion of the 2014 Super Rugby season, but in May 2014, he was released early from his contract by the Crusaders due to his poor fitness.

[27] Guildford accepted the offer in August, but a week later stated that he may not move to the Waratahs in order to stay closer to his family and friends,[23] and instead play Super Rugby for a New Zealand-based team, with coach Tana Umaga showing interest in signing him for the Blues.

[28] Despite the speculation, the Waratahs announced that they had signed Guildford on a ten-month contract in September and was due to move to Sydney at the end of October.

[30] Guildford was dropped mid-season from the Waratahs squad, forcing him to play in the Shute Shield for West Harbour RFC, but later earned a recall into the team.

[32] Tasman announced in May that they had signed Guildford for the 2016 Mitre 10 Cup season to replace injured wings Viliami Lolohea and James Lowe.

[37] Through their mutual ties to Hawke's Bay, coach Roger Randle influenced Guildford to move to Waikato at the end of 2016.

[47] Guildford represented New Zealand at the 2007 U19 Rugby World Cup in Belfast,[5] and started in all of the sides five games at the tournament,[13] and scored three tries.

[13] Guildford played for New Zealand in the 2009 Junior World Championship hosted in Japan as the only returning player from the previous year's side.

Starting on the left wing, Guildford played the entire match as the All Blacks won 12-19,[52] his performance including a try-saving tackle against lock Alun Wyn Jones.

[55] He was then selected for the 22-man trial squad for New Zealand's 2010 Commonwealth Games sevens team,[56] meaning that Guildford would not play in the All Blacks' northern hemisphere tour too.

[55] After a poor performance against Australia and a late-night drinking session that followed, Guildford's chances of being selected for the All Blacks' 2011 Rugby World Cup squad looked to be remote.

[58] A hamstring injury to Richard Kahui presented him an opportunity to be chosen for New Zealand's final pool match against Canada, where he scored four tries in the All Blacks' 79–15 victory.

[61][62] On that night, police were called after receiving a complaint that Guildford and another man were arguing and fighting on the side of the road about who had lost the key to their scooter.

[63] Naked, and bleeding from a wound to his forehead, Guildford walked into Trader Jack's restaurant and punched one man that asked him if he needed help.

[70] A month prior to the sentencing for the fraud charges, he was convicted and discharged for breaching an intensive supervision order by drinking alcohol.