2013: Started five of 10 appearances in second MLS season, logging 430 minutes. Started and went a full 90 minutes in 0-0 draw vs. NE (4/13). Started both legs of CCL Semifinals against Santos Laguna, including a nod at forward in first leg (4/2) and a full 90 minutes at left midfield in second leg (4/9). Appeared in 14 games across all competitions, starting nine. Started all seven MLS Reserve League appearances, logging 522 minutes.
2012: Made big impact in his first MLS season, finishing third on the team with four assists in MLS play and seven across all competitions. In his first career start, he recorded his first assist when his corner kick found Zach Scott for the game-winner in a 1-0 win vs. COL (4/14). He picked up an assist in a 2-0 win at DAL (5/9), then came off the bench to assist on David Estrada’s equalizer in a 1-1 draw at CHV (5/26), and recorded his second game-winning assist of the year at COL (7/28) in a 2-1 win. Caskey scored his first career MLS goal in a 4-0 win vs. LA (8/5) when he chipped the keeper from 30-yards out. Outside of MLS play, he scored two goals and three assists in U.S. Open Cup and CONCACAF Champions League play, most notably recording a goal and assist in a 3-1 win at Caledonia AIA (8/30).
>h3>OTHER PROFESSIONAL EXPERIENCE
2011: Spent the 2011 season with the Charleston Battery of the USL. He appeared in 22 games, starting 15, and logging 1299 minutes. He scored one goal and recorded one assist. His lone goal of the season was a game winner that came in a 1-0 over Orlando City on 7/9/11.
2010: Started all 20 games as a senior, scoring a career best 18 points with seven goals and four assists. Named to the NCCSIA All-State Team. Served as co-captain for second straight year. Named to NSCAA All-South Region second team for second consecutive season and All-Southern Conference first team for third consecutive season. Named to the 2010 SoCon All-Tournament team. Earned second straight selection to the North Carolina Collegiate Sports Information Association All-State team. Did not miss a match in his four-year career, finishing with 76 starts. Voted MVP by his teammates.
2009: As a junior, he was named to the 2009 All-Southern Conference first team, earned a place on the NSCAA All-South Region second team and NCCSIA All-State team. Tied career-high with seven goals and added two assists. His 16 points were sixth best in the conference. Named Southern Conference Player of the Week honors and earned place on both the Soccer America and College Soccer News Teams of the Week for his brace in a 4-1 upset win over No. 25 South Carolina. Only subbed out of two games, logging 1622 minutes.
2008: Named to the 2008 All-Southern Conference first team as a sophomore. Led the team with 1,681 minutes of action as well as assists with four. His three goals scored were tied for top on the team. 22 of his 33 shots were on goal.
2007: Started a team-high 19 matches as a freshman. Recorded two goals and five assists, scoring his first career goal against nationally-ranked Furman. Put 11 of his 20 total shots on goal for a team-high .550 shots on goal percentage.
Signed on March 4, 2014 via a trade with Seattle Sounders FC.