Lindsey played at the University of Virginia from 1998 to 2001 and was the school’s first-ever Atlantic Coast Conference Player of the Year, winning the award two consecutive years (2000 & 2001) joining Mia Hamm as the only other player to achieve that distinction. She finished sixth all-time scorer in UVA history with 33 goals and 76 points and was named NSCAA Second-Team All-American in 2001 and Third-Team All-American in 2000. She was also a 2001 finalist for the M.A.C. Award. Lindsey was named Female Athlete of the Year at UVA for the 2001–02 academic year.

Lindsey played for the Indiana Blaze of the W-League from 1997 to 2000. In 2002, she was the fourth overall pick in the WUSA draft by the San Diego Spirit. She played in 20 games, starting 13 and scored two goals with five assists. She was traded to the Washington Freedom during the 2003 WUSA Draft and was a member of 2003 Founders Cup III Champions.

In 2009, she played for the Washington Freedom in the inaugural season of the WPS after being taken 17th overall by the Freedom in the WPS General Draft. She started 18 of the 19 games she played for the Freedom, scoring two goals with one assist.

Lindsey was called into national team training camps in 2009 and 2010 and was in Residency Training Camp at the Home Depot Center in 2004 and 2006. She played one match in the 2011 FIFA Women’s World Cup in Germany against Colombia which the U.S. won 3–0. She has been described as one of the best possessors of the ball on the U.S. team and is known for her excellent work rate, superb passing, and willingness to sacrifice for the team. As a central midfielder, she led the team in assists in 2010 with seven.

Lindsey resides in Washington, D.C. She came out publicly as gay in 2012 in an interview with Autostraddle, but notes her sexuality has never been in question to friends and family.

In January 2013 Lindsey was allocated to the Washington Spirit in the newly formed National Women’s Soccer League. She started 21 games and captained the team in 2013. Following the 2013 NWSL season, she went on loan to Canberra United in the W-League.

In 2014 Lindsay played in 22 games for the Spirit. After the NWSL season, she again went on loan to Canberra United. Canberra won the 2014 W-League Championship by defeating Perth Glory in the Grand Final.

Lindsay announced in August 2014 that she would be retiring at the end of the year.

On April 24, 2017 it was announced that Lindsay would join the staff of the Washington Spirit Development Academy as the Strength and Conditioning Director and Assistant Coach.

In 2018 Lindsay served as a commentator for non-televised NWSL games that were broadcast on go90 and the NWSL website.

Nashville SC in 2020 announced Lindsay would serve as its sideline reporter.