As a youth, Condra played in the 2000 Quebec International Pee-Wee Hockey Tournament with the Detroit Honeybaked minor ice hockey team. Condra played junior hockey with the Texarkana Bandits of the NAHL in 2003–04, where in 56 games, he scored 20 goals and 44 points to lead the club in points. He moved to the Lincoln Stars of the USHL for the 2004–05 season. In 60 games with Lincoln, Condra tied for the team high with 30 goals, while finishing second on the club with 60 points, helping the Stars to a playoff berth. In four post-season games, Condra had two assists. Condra joined the Notre Dame Fighting Irish of the CCHA for the 2005–06 season. As a freshman, Condra had six goals, and a team high 34 points in 36 games with Notre Dame, and placed him on the All-Rookie team of the CCHA. After the season, the Ottawa Senators drafted Condra with the 211th overall pick in the 2006 NHL Entry Draft. While at Notre Dame, Condra studied pre-med in psychology. His offensive numbers improved in the 2006–07, as Condra once again led the Fighting Irish in points, as he scored 14 goals and 48 points in 42 games. In 2007–08, Condra led the team in scoring once again, scoring 15 goals and 38 points in 41 games played. Condra finished his collegiate career in 2008–09, leading Notre Dame in scoring for the fourth consecutive season, as he scored 13 goals and 38 points in 40 games.
Professional
Ottawa Senators
After a very successful college career, the Ottawa Senators assigned Condra to their AHL affiliate, the Binghamton Senators for the 2009–10 season. In his first professional season, Condra had 11 goals and 38 points while appearing in all 80 games for the Senators. However, Binghamton failed to reach the playoffs. Condra began the 2010–11 season with Binghamton, scoring 17 goals and 47 points in 55 games before being called up by the Ottawa Senators. He made his NHL debut on February 15, 2011, recording an assist in a 4–3 shootout loss to the New York Islanders. Condra scored his first NHL goal on February 26, 2011, scoring twice against goaltender Brian Boucher in a 4–1 win over the Philadelphia Flyers. He had another two goal game on March 8, 2011, against Martin Brodeur as Ottawa defeated the New Jersey Devils 2–1. In total, Condra registered six goals and 11 points in 26 games with Ottawa. After Ottawa's season concluded, Condra was sent back to Binghamton for their playoff run, where he scored five goals and 17 points in 23 games, as the Senators won the 2011 Calder Cup. In his first full NHL season, Condra earned a regular roster spot in Ottawa. Though he struggled offensively at times, he established himself as a dependable defensive forward and recorded 8 goals and 25 points in 81 games. During the 2012 NHL Lockout, Condra spent time with the Fussen Leopards, a third division club in Germany. After dominating at that level, he moved up to the second-tier league Eishockey-Bundesliga, joining fellow NHLers Matt D'Agostini and Rick DiPietro with SC Riessersee.
On July 1, 2015, Condra signed a three-year deal with the Tampa Bay Lightning, which has a $1.25 million annual average. Condra has previous ties to Lightning head coach Jon Cooper, who he played for while Cooper was coach of Texarkana of the NAHL. On October 8, 2015, Condra played in his 300th career NHL game in a 3–2 OT Lightning victory over the visiting Philadelphia Flyers. Condra also took part in the first ever 3 on 3 regular season overtime game under the new overtime format during that same game. On March 17, 2017, Condra was named the captain of the Syracuse Crunch. Condra became the 20th full-time captain in Crunch franchise history and the third since Syracuse became the affiliate of the Tampa Bay Lightning in 2012.
After three seasons within the Lightning organization, Condra left as a free agent and agreed to a one-year, two-way contract with the Dallas Stars on July 1, 2018. After attending Dallas' training camp, Condra was placed on waivers and re-assigned to AHL affiliate, the Texas Stars to begin the 2018–19 season. As an alternate captain with Texas, Condra added a top-line veteran scoring presence. On January 4, 2019, Condra was recalled by Dallas and appeared in his first NHL game since 2017, in a 2-1 overtime victory over the Washington Capitals. He notched his first goal, providing the Stars only goal in a 3-1 defeat to the St. Louis Blues on January 12, 2019. After 6 games and with the Stars returning to health, Condra was returned for the remainder of the season to Texas. He led the team in regular season scoring with 20 goals and 54 points in 71 games.
Colorado Eagles
As a free agent from the Stars, Condra agreed to continue his career in the AHL, signing a one-year contract with the Colorado Eagles, affiliate to the Colorado Avalanche, on July 22, 2019.
