[citation needed] At the age of 19, Riddle was the youngest member of Bobby Clark's 1996 New Zealand Olympic Team, where he made four appearances including one as a substitute, in a 1–0 victory over then Oceania rivals Australia.
[citation needed] After brief stints with several clubs including Chelmsford City in the UK, Riddle turned to the US college system and spent two years with the Myrtle Beach-based Coastal Carolina University before being signed by Kiwi football icon Wynton Rufer for the Kingz debut season in the National Soccer League in 1999.
[3][4] Although he signed a two-year contract, Riddle struggled to regularly feature in the Kingz side and only managed nine appearances with a return of two goals, both of which came away from home against Adelaide United and Brisbane Strikers.
[citation needed] Riddle guided his side to second place in the Central Conferences Midwest Division narrowly finishing behind the Chicago Fire Premier in the regular season standings.
[citation needed] The teams run would continue under Riddle and they defeated perennial USL Premier Development League powerhouse the Michigan Bucks[who said this?]