Incollingo began his career in 1997, with Vermont Voltage of the USISL D-3 Pro League.
[3] In his debut season with Montreal he helped the club finish second in the Northeast division, and reach the Conference semi-finals in the playoffs.
[4] In 2001, he was re-united for the third time with Jankovic who became the new head coach for the Montreal Dynamites of the Canadian Professional Soccer League and signed him to a contract.
[5][6] With the Dynamites he served as the team captain and helped Montreal finish fourth in the overall standings.
He also played indoor soccer in the National Professional Soccer League having stints with Milwaukee Wave where he appeared in a total of fourteen matches, and also played with Montreal Impact's indoor squad appearing 17 matches.