Four Rochdale sex gang members face deportation to Pakistan after immigration judges rejected their citizenship appeal.
The gang had appealed a decision by Theresa May, made during her time as Home Secretary, to strip them of British citizenship as a first step to their deportation.
The four men - Shabir Ahmed, Adil Khan, Qari Abdul Rauf and Abdul Aziz - were convicted in 2012 of grooming girls as young as 13 in Rochdale, a town in Greater Manchester.
Ahmed, the ringleader of the group, is serving a 22-year jail sentence after being convicted of a list of offences in 2012.
The judge overhearing the case, Justice Bernard McCloskey, accused the lawyers representing the gang of "frankly shameful" behaviour, saying they had failed to submit the necessary documentation and asked for several adjournments in a bid to obstruct the deportation process.
McCloskey said: "The Upper Tribunal has been treated with sustained and marked disrespect. The conduct of these appeals has been cavalier and unprofessional. The rule of law has been weakened in consequence."