During his college years he also played with Thunder Bay Chill in the USL Premier Development League, and was part of the Chill squad which won the 2008 PDL championship title.
Their fairytale run would continue under Riddle and they defeated perennial USL Premier Development League powerhouse the Michigan Bucks on 26 July to advance to the national quarter finals where the Thunder Bay Chill would end the Outrage's season.
The second half of the season, in which the majority of the games were played at Chapples Park, generally turned more in Thunder Bay's favor: they overpowered Wisconsin Rebels 4-1, and sneaked a 5-4 victory over Des Moines off an injury-time winner from Doco Wesseh, but lost both of their two final regular season games at home to Chicago Fire Premier.
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Western Conference champions Vancouver Whitecaps Residency travelled to Chapples Park for an all-Canadian national semi-final; Alvaro Zendejas scored a 90th minute winner in front of 1,546 fans to send Thunder Bay to the PDL Championship game for the first time.
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Chill's form improved once they returned home to Chapples Park, overturning Fort Wayne 5-1 off a hat trick by Josiah Seton, registering a hard-fought 2-1 come-from-behind win over Des Moines, and emerging victorious from a bruising 5-3 encounter with Sioux Falls.
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