A federal court judge on Friday denied a motion for an injunction by Dream Nite Club owners, who were seeking to reverse the non-renewal of their liquor license.

“We believed this motion had absolutely no merit, as the judge has held,” said Ann Arbor City Attorney Stephen Postema.

The nightclub was evicted from its former location on South Fourth Avenue on May 9.

A few days before, on May 4, Dream Nite Club owners filed an “emergency” motion asking the U.S. District Court in Detroit to reverse a March 21 decision of the Ann Arbor City Council to not renew their liquor license.

After an hearing that same day, Judge Paul Borman declined to accept the “immediate temporary restraining order” the owners were seeking in regard to their liquor license. Instead, the judge requested a “further, expedited hearing from both parties,” according to court records.

Court records show V.R. Entertainment - comprised of Vickash Mangray, Jeff Mangray and Moonie Mangray - made several legal mishaps throughout the process.

Two motions were actually filed on May 4, with a slightly different title.

“Aside from this difference in title, the motions are identical,” court records said. “Plaintiff’s counsel made no effort to withdraw the duplicate motion.”

The court subsequently struck one of the motions for docket efficiency.

On May 9, V.R. Entertainment filed two documents entitled “Plaintiff’s response to defendant’s answer.” They had to amend it that it was a reply to a response.

Then instead of a customary five-page reply, V.R. Entertainment filed a 21-page reply.

“The court finds that the arguments raised by defendants … do not warrant a 21-page reply brief,” court records said.

Ultimately, the nightclub didn’t meet any of the legal requirements to get the liquor license back.

The matter will appear again in federal court on May 30, when the judge could dismiss a $3 million lawsuit filed against the city.