Kevin Winter/Getty Images via ABCMadonna has lost her bid to block some of her personal items – including a break-up letter from late rapper Tupac Shakur — from being sold at auction.

According to the New York Daily News, a Manhattan Supreme Court Judge ruled Monday that Madonna’s former friend Darlene Lutz was free to sell the possessions.

The singer had sued Lutz last July to prevent her from profiting off the items, which also include a pair of used panties and a used hairbrush. But Judge Gerald Lebovits ruled that because Madonna signed a release in 2004 allowing Lutz to keep some of her things, she did not have grounds to sue.

“[Madonna] knew that throughout her relationship with Lutz, Lutz was in possession of various pieces of [Madonna’s] personal property,” the judge wrote in his decision, according to the Daily News. “Yet before this action began, the plaintiff did not make any demand to return her possessions.”

Madonna had claimed that she didn’t know Lutz had possession of the Tupac letter, which was personal in nature. Tupac and Madonna dated from 1993 to 1994. The rapper wrote her the letter from jail in 1995 and included details of their breakup.

The items will go up for bid in July on

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