Undrafted by MLS, Conrad had an unsuccessful trial with the Los Angeles Galaxy. However, the Galaxy coaching staff recommended he play for one of their affiliated lower division teams. Consequently, Conrad contacted the now-defunct San Diego Flash of the A-League which gave him a contract. In 1999, Brian Quinn became the head coach of the San Jose Clash. When Quinn began searching for an additional defender and goalkeeper for the Clash, Ralf Wilhelms, head coach of the Flash and a former teammate of Quinn on the San Diego Sockers, recommended Conrad and Flash goalkeeper Joe Cannon. The Flash signed Conrad that year. He played with the club, later re-branded as the Earthquakes, for four seasons, helping them to the MLS Cup in 2001. In 2000, he also played for Lech Poznań in Poland. In 2003, Conrad was traded to the Wizards for a second-round draft pick, which the 'Quakes used to select Arturo Alvarez. Conrad's stock rose while with Kansas City; never a big scorer, he tallied four goals during his first season (he has ten in his MLS career). In 2004, he helped the Wizards to the US Open Cup and the MLS Cup Final as the leader of the league's stingiest defense and was named to the league's Best XI and was a finalist for MLS Defender of the Year Award. He won the award a year later.
Despite rumors of a possible European transfer following the Wizards' disappointing 2006 season, Conrad renewed his contract with the Wizards beginning the 2007 season, and new head coach Curt Onalfo rewarded him the club captaincy.
Conrad was out of contract after the 2010 MLS season and elected to participate in the 2010 MLS Re-Entry Draft. On December 15, 2010 Conrad was selected by Chivas USA in Stage 2 of the Re-Entry draft. He made his debut, and scored his first goal for his new team on March 19, 2011 in their first game of the 2011 MLS season – ironically against his old club, Sporting Kansas City.
After struggling with injury during the 2011 season, and suffering from side effects of six concussions, Jimmy Conrad announced his retirement from professional soccer on August 18, 2011.
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