Sampson began his career in 2006 with Windsor Border Stars of the Canadian Soccer League.
[3][4] He helped Windsor clinch a postseason berth by finishing third in the National Division.
[5] In the second round of the postseason the club was eliminated from the competition after losing to Serbian White Eagles.
[6] The Detroit Ignition of Major Indoor Soccer League (MISL) drafted Sampson in 2006.
Sampson played the 2010–11 MISL season for the Baltimore Blast, scoring 8 goals and 8 assists in 14 regular games.