Lynn Tonks had been on a night out at the New Moon pub in Bristol when she decided a man, who was with two friends, had given her a dirty look.
The court heard how the Blue Arrow Recruitment manager first walked up to Simon Dove and slapped him across the face.
He rowed with the 50-year-old, who regularly helped out charities, but later left the pub.
In court, jurors heard that Tonks was then seen pouring her wine onto the floor and hiding the empty glass in her pocket.
She then also left the pub, where witnesses said she held the glass and punched a second man, Ashley Williams, in the face.
The blow caused the glass to shatter, leaving just the stem and one shard remaining.
Witnesses said that the boss then punched Mr Dove – leaving a large gash, containing fragments of bone, above his eye.
The strike also cracked his eye socket.
According to the Bristol Post, Tonks told witnesses at a bus stop: ‘I’m 50 years of age, I don’t need this shit. You don’t know the half of it, he punched me in the pub.’
Tonks denied the offences but was found guilty and jailed for three years.
She was convicted of wounding and causing actual bodily harm.
After the case, Detective Constable Haley Matthews said: ‘The fact Tonks was intoxicated was no excuse for the level of violence she used against her victims.
‘In using a glass as a weapon, she not only inflicted significant injuries but she also left her victims with permanent scars, which they now have to live with every day.’