Joe Anderson failed in his attempt to seek a judicial review into his arrest on suspicion of bribery and witness intimidation.
The former Mayor of Liverpool brought proceedings against Merseyside Police in March, following his arrest in December 2020.
The application was rejected and he then lost an appeal against that initial decision.
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Mr Anderson was arrested along with four other men when officers swooped on addresses across the city late last year.
The arrests formed part of Operation Aloft, an ongoing investigation into building and development contracts in Liverpool.
The 63-year-old, who stepped down from his role as mayor in the aftermath of his arrest, has denied wrongdoing.
Earlier this year he turned to the courts in a bid to have his arrest and the searches of premises associated with him declared unlawful.
However, the judicial review bid was first rejected by Mr Justice Julian Knowles. A second judge, Mr Justice Ian Dove, then upheld the initial decision in July after it was appealed by Mr Anderson.
A spokesperson for Merseyside Police confirmed Mr Anderson had issued proceedings against the chief constable of the force, focusing on his arrest and the property searches.
The force said: "As part of this he argued that as a matter of law, on the facts in the matter, his actions could not amount to witness intimidation.
"As is usual in judicial review proceedings the matter was considered on paper and Mr Justice Julian Knowles refused Mr Joseph Anderson permission to bring judicial review proceedings on all grounds.
"Mr Joseph Anderson sought an oral renewal hearing, as is his right in such proceedings.
"The matter was heard before Mr Justice Dove in July 2021 in the Administrative Court sitting in Manchester.
"Mr Justice Dove again refused Mr Anderson permission to bring judicial review proceedings, as such the arrest and searches of Mr Joseph Anderson’s premises were lawful. Mr Joseph Anderson was ordered to pay costs to the chief constable.”
Earlier this year, Mr Anderson also brought action against Liverpool Council for refusing to provide indemnity to cover the legal costs of defending himself against the allegations that formed part of the police investigation.
In that case, High Court judge Mrs Justice Yip said the council had wrongly applied its own policy when making the decision not to grant the indemnity.
The hearing, which also took place in July, heard that the council's decision not to grant the indemnity to Mr Anderson was made because it would not have been lawful to do so, and that the allegations against him did not relate to work he carried out in his position as Mayor of Liverpool.
The judge said the authority had wrongly applied the policy and should reconsider the request.
The ECHO understands a final decision on the matter has not yet been reached by the council.
Mr Anderson was approached for comment.
