Condra took a route to the NHL that has become increasingly common. The Michigan-born forward started in the lower junior leagues, working through college and the minors before reaching the top level.

The first stop was Texarkana, Texas, in the North American Hockey League, where Condra played under Tampa Bay Lightning head coach Jon Cooper. Condra led Texarkana in scoring in 2003-04 and later that summer was an usher in Cooper's wedding.

Condra made the jump from the NAHL to the United States Hockey League for the 2004-05 season to play for Lincoln. A year later, Condra moved to the college ranks with Notre Dame.

Condra's game began to evolve and he gained the attention of NHL scouts. Having been passed over in his first eligible draft year, Condra went on to lead the Fighting Irish in scoring with 34 points in 36 games as a freshman in 2005-06 and was named to the Central Collegiate Hockey Association's all-rookie team. He was selected by the Ottawa Senators in the seventh round (No. 211) of the 2006 NHL Draft.

Condra spent three more seasons at Notre Dame, where he led the Fighting Irish in scoring each of his four years before turning pro at the age of 23.

In 2011-12, his second season in the Ottawa organization, Condra earned his first call-up to the NHL, appearing in 26 games before finishing the season playing in the AHL playoffs. He helped Binghamton capture the Calder Cup, picking up 17 points in 23 playoff games.

During the 2012-13 season, Condra was a regular in the Ottawa lineup, and in 2014-15 he helped the Senators charge into the Stanley Cup Playoffs on a 23-4-4 run in the final 31 games. The Senators finished seventh in the Eastern Conference after sitting 14 points back Jan. 31.

On July 1, 2015, Condra joined the Lightning as a free agent. He signed a three-year contract and was reunited with Cooper.