Caugherty grew up in Pittsburgh, Pennsylvania and attended Penn Hills High School, where he was named Section Player of the Year, All-WPIAL, All-State, and All-American.

He played club soccer for Penns Forest and Pittsburgh Beadling, respectively, leading the latter to the national championships his senior year.

Soon after being drafted by the Wizards, Caugherty moved to Denmark and signed with Odense-based club B 1909, a Danish second division team, before the start of the 2005 MLS season.

In his first pre-season game with the club Caugherty scored a goal but then later suffered an ankle injury on artificial grass which jeopardized his career.

[3] It was announced on August 28, 2008, that Caugherty had moved from the Riverhounds to FC Unirea Alba Iulia of Romania, who play in Liga II in 2008–09.

[4] However, Caugherty resurfaced in the United States again in 2009, and after a trial with Seattle Sounders FC, signed with USL First Division expansion franchise Austin Aztex.