Takahara was born in Mishima on June 4, 1979. After graduating from Shimizu Higashi High School, he joined J1 League club Júbilo Iwata in 1998. In 1998, the club won J.League Cup and he was selected "New Hero awards". In 1999, the club won J1 League and 1998–99 Asian Club Championship. The club also won the 2nd place 1999–00 and 2000–01 Asian Club Championship. In August 2001, he moved to Boca Juniors on loan. In February 2002, he returned to Júbilo Iwata. The club won the champions and he became a top scorer with 26 goals in 27 matches. End of 2002 season, he moved to German Bundesliga club Hamburger SV. In 2006, he moved to Eintracht Frankfurt. In 2008, he returned to Japan and joined Urawa Reds. However his opportunity to play decreased in 2010 and he moved to K-League club Suwon Samsung Bluewings in July. In 2011, he returned to Japan and joined Shimizu S-Pulse. From 2013, he played for Tokyo Verdy, SC Sagamihara and Okinawa SV.