Francis 'Fraggle' Green, 30, and Robert Daniel, 22, viciously assaulted Susanne Simpson, 43, outside the Cairn Bar in Balornock, in the north of the city, on October 23, 2011.
After a trial at Glasgow Sheriff Court the men were found guilty of assaulting Miss Simpson to her severe injury.
Sheriff Bill Totten told them: "You have both been convicted by the jury in this case of a brutal attack on a defenceless female that resulted in her severe injury and at the time of the incident you were on bail."
Daniel was jailed for three years and Green was sentenced to three and a half years.
Miss Simpson had been drinking with friends and had spoken to Green's sister Kelly, partner of gunned down gangster Kevin 'Gerbil' Carroll and daughter of crime boss Jamie Daniel.
Moments later four hooded men appeared in the bar including Green, from Milton of Campsie, East Dunbartonshire and Daniel, of the city's Springburn, also a member of the family.
Miss Simpson made her way outside to talk to Green when Daniel butted her, knocking her to the ground and she was dragged to a darker area by the bar, and punched and kicked.
Green denied the charge and claimed to have no involvement in the fight and Daniel claimed to be one of the other men who did not do anything.
But the whole incident was caught on CCTV.
Miss Simpson was left with a fractured cheek and damage to her scalp
The jury was asked to convict both men. Green was described as the "catalyst" who assisted in the attack while Daniel head butted Miss Simpson, dragged her along the ground and continued the attack.