An arbitrator has denied Rimas Sports' request for a temporary restraining order that would have allowed its main baseball agent, William Arroyo, to continue representing clients while navigating an appeal of his decertification, ESPN has learned.

The decision was made by arbitrator Michael Gottesman on Friday. On Monday, the Major League Baseball Players' Association made the procedural step of filing a motion with the Southern District of New York asking that the court uphold his decision.

Arroyo originally had his agent certification revoked on April 10 in the wake of an MLBPA investigation about improper benefits provided to players.

Jonathan Miranda and Noah Assad, two prominent executives for the Bad Bunny-led agency, were also denied their applications for certification. 

Michael Velazquez, another certified agent who recently joined Rimas, must leave the agency by May 10 or face potential decertification, sources with knowledge of the situation said.