[4] During his time in college, Ockford also played in the USL Premier Development League for Central Jersey Spartans and Reading United.
[8][9] On May 28, Ockford made his professional debut and scored his first goal in a 2–0 win over NPSL club Brooklyn Italians in the third round of the Lamar Hunt U.S. Open Cup.
[11] Ockford scored two goals and made 10 appearances for the Cosmos during the 2014 regular season, helping the team clinch a berth in The Championship.
[19] Ockford was signed by the San Jose Earthquakes on December 14, 2017, along with Reno teammates Chris Wehan and Luis Felipe Fernandes.
[20] He made his MLS debut on March 3, 2018, during San Jose's season-opening 3–2 victory over Minnesota United FC, substituting on in the 54th minute after Yeferson Quintana was injured.