Early in his ministry he worked closely with Glen and Larry McLean. He was based in Eston, Saskatchewan from 1980 to 1988, but in September 1988, he and his family moved from Canada to southern California. He worked on the staff for Calvary Chapel Costa Mesa for about three years. After forming Understanding the Times International in 1990, he was led to spread the gospel world-wide.

Calvary Chapel Termination

After writing an article entitled Ichabod, Roger Oakland was stricken from Calvary Chapel's radio network/station, KWVE November 19, 2007. Understand the Times International had been broadcasting Monday through Friday for 15yrs and its removal had profound impacts.

Nearly Fatal Accident

On July 20, 2009 Roger Oakland had a fall which broke his ribs, and punctured his lungs. Emergency surgery was performed.He is still recovering and has returned to Eston, Saskatchewan.