Prince Andrew has a crisis looming over his head as his court hearing reportedly couldn't have gone any worse for him.

A case was filed in the US against the Duke of York by Virginia Giuffre last year for allegedly having sex with her three times while she was still a minor and was being trafficked to him by convicted pedophile Jeffrey Epstein. In the latest court hearing in New York on Monday, the legal team of the British royal made another attempt to have the case thrown out on the grounds that Giuffre had waived her right to sue Andrew when she signed an earlier £370,000 ($500,000) private legal settlement with Epstein in 2009.

However, Judge Lewis Kaplan put Andrew's legal team through a bruising encounter during the make-or-break hearing, and did not seem to accept most of the arguments by the Duke's lawyer, Andrew Brettler. The judge said that the part of the settlement between Epstein and Giuffre protecting "other potential defendants" that Andrew's lawyers are basing their case on was "unclear." He also pointed to two sentences in the text that seemed to suggest it could not apply in Andrew's case, reports The Times.

He also noted that the language in the agreement which states that it is "not intended to be used by any other person" to protect themselves from lawsuits without the agreement of Epstein and Giuffre means Andrew cannot rely on it. The judge did not immediately give his ruling at the end of hearing, and told the royal he would find out his decision "pretty soon,' most likely within days.

However, legal expert Mitchell Epner believes that Judge Kaplan's comments during the hearing suggest that Andrew's hopes to have the case thrown out of court are hanging by a thread. The former federal prosecutor added that the hearing in the case "could not have gone worse" for Andrew.

Epner noted that Andrew's legal team was reduced to saying they "respectfully disagree" with the judge, which is not a good sign as "respectfully disagreeing with the judge means you are about to lose." Other sources close to the virtual proceeding also described it as "brutal" for the British royal, pointing out that the judge interjected his lawyer several times when he was presenting his arguments.

In addition, Judge Kaplan ordered that the exchange of potential evidence in the case was to proceed as scheduled, which suggests that Andrew's request to have the case closed would most likely be dismissed.

Prince Andrew
Main developments surrounding the sexual assault lawsuit filed against Prince Andrew. Gal Roma/AFP