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Henderson completed his Dartmouth College football career with 67 games played, starting 53 of those. He tallied 53 career points on 20 goals and 13 assists and scored eight game-winners. Henderson earned All-Ivy and All-Northeast second team honors his senior year despite an injury that held him to just 11 games played this fall. After being named the unanimous Ivy Player of the Year and an All-America selection in 2008, Henderson was cut down just nine games into this season. As a senior, he posted 12 points on four goals and four assists.
In August 2009, Henderson spent a week training with the Swedish topteam Kalmar FF. Although he was not signed by Kalmar, he made a good impression and in an interview post Henderson's trial, a Kalmar FF spokesperson mentioned the possibility of signing Henderson in future.
In December 2009 Henderson signed a three-year contract with the Swedish 1st Division Club, Mjällby AIF, who were promoted from the Swedish 2nd Division at the conclusion of the preceding season. He began his appointment with the club in January 2010. Specific terms of the contract are undisclosed, but include a signing bonus, salary and other stipends.
On 26 February 2010, Henderson suffered a knee injury which while in pre-season training with Mjällby AIF which prevented him from making his All Whites debut against Mexico the following week. A scan later revealed a ruptured Anterior cruciate ligament which required surgery, keeping Henderson out of all football for six to eight months, ending his hopes of representing New Zealand at the 2010 FIFA World Cup.