Madonna has lost her legal battle to stop the sale of the letter Tupac sent her when they broke up.
A Manhattan Supreme Court Judge has ruled that Madonna's former friend Darlene Lutz would be able to sell on personal items belonging to the singer because the statute of limitation to recover items had passed.
In giving his decision, Justice Gerald Lebovits shared: "[Madonna] knew that throughout her relationship with Lutz, Lutz was in possession of various pieces of [Madonna's] personal property. Yet before this auction began, the plaintiff did not make any demand to return her possessions."
Whilst Gotta Have It! online auction house co-owner Ed Kosinski added: "It's a clear cut victory for us. She shouldn't have signed a settlement agreement relinquishing the right to all property in Darlene's possession."
In 2004, Madonna had also signed a release from "any and all" future claims against Lutz, meaning she could not bring this lawsuit.
Other items included in this collection were silk underwear belonging to the star and a hairbrush with strands of her hair.
Madonna previously insisted her love letter shouldn't be sold because it was "intensely personal".
She recalled: "I have a specific memory of receiving that letter because I had a close personal relationship with Tupac Shakur and I specifically remember receiving a phone call from him while he was in jail. My recollection is that he had one of his friends hand deliver the letter to my home in Manhattan.
"I also have a specific memory of reading the letter. In particular, I remember that he apologised to me. I never gave this letter away. It is intensely personal."
The items - including the letter - will go back up for sale in July.