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On February 4, 2015 Segares announced his retirement. He remained on staff with Chicago Fire as an academy coach and a club ambassador.

After the 2009 season, Segares left the Fire for Greek Cypriot club Apollon Limassol. 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.

Earning his first call up in 2007, he participated in 2010 FIFA World Cup qualifying and the 2009 CONCACAF Gold Cup where Costa Rica made it to the Semifinals.

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.

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.

Gonzalo Segares González (born October 13, 1982 in San José) is a retired Costa Rican footballer who spent most of his career with the Chicago Fire in Major League Soccer. He currently serves as head coach for the United States under-15 national team.