Youth and college Segares started his career playing in
Saprissa's minor league system, before being awarded with a scholarship to play
college soccer at
Virginia Commonwealth University from 2001 to 2004. Segares was a strong player from his debut, starting all 83 games he played in his four seasons. He registered 16 goals and 10 assists from the back in his four years with the team, was a first-team All-CAA selection his final three years, and was a first team
All-American and
Hermann Trophy finalist as a senior. During this time he also played with the
Williamsburg Legacy in the
USL Premier Development League.
Professional Segares began his professional career with the
Chicago Fire as a 2005 SuperDraft third round selection, and quickly proved himself during his rookie campaign. Segares was in the Fire's starting eleven for the first three games of the 2006 campaign until an ankle injury sidelined the young defender for a month of action. Upon his return, Segares came back with a vengeance, starting 19 of Chicago's last 24 games. Segares also helped the "Men in Red" earn an MLS club-record fourth
Lamar Hunt U.S. Open Cup title in 2006, playing every minute in the tournament's Final. He held down the left side of defense in Chicago's starting XI in 2008 and 2009, while balancing his burgeoning duties for both club and country. After the 2009 season, Segares left the Fire for Greek Cypriot club
Apollon Limassol on a free transfer. In August 2010 Segares returned to the Fire. On December 6, 2012 Chicago Fire re-signed Segares to a multi-year deal. At the end of the 2014 season, the club declined his contract option. On February 4, 2015, Segares announced his retirement.
International Earning his first call up in 2007, Segares participated in
2010 FIFA World Cup qualifying and the
2009 CONCACAF Gold Cup, where Costa Rica made it to the semifinals. ==Coaching career==