Kane Buckley, 26, will spend 30 months behind bars for his involvement in a fight that saw Southampton FC and Tottenham Hotspur fans clash.
Buckley, who worked full-time and cared for his vulnerable grandmother, planned the incident on March 18, 2023, with Spurs supporter Dante Lauder-Hawkins.
But this is not the first time he has been embroiled in football-related violence, Southampton Crown Court heard.
Prosecutor Simon Jones told the court that Buckley was known to police officer as he had been involved in five other incidents before the one in March 2023.
The court was shown videos of Buckley threatening fans on the opposing side after Saints games.
“Here he can be seen with a Burberry scarf pulled up over his face”, Mr Jones told the court.
On one occasion in 2022, he attempted to fully conceal his identity by wearing a balaclava, and after attending a Southampton v Leeds match, he was told to “get away” from Leeds supporters by police.
A video was also shown of the 26-year-old leading the charge when Southampton played Portsmouth, threatening Portsmouth fans and chanting.
Speaking on his organisation of the fight in Southampton in March of 2023, Mr Jones said: “When Kane Buckley was arrested on April 6, 2023, it was clear he had been reluctant to hand over his mobile phone.
"The police suspected he had hidden it and after a search, found it under his bed.
"Officers discovered he had been in contact with Dante Lauder-Hawkins, a Spurs supporter who has pleaded guilty to violent disorder.
"The fact there is contact between the two rival groups is important."
But, mitigating, Charles Gabb said Buckley had little involvement in the violence.
He said: “Mr Buckley was only involved in the first phase of the violence, after which he runs away and is not seen at the Mail Room, or the brawl which spilled into the road.
"He does not use any overt violence, and he runs away", he added.
Judge Nicholas Rowland interjected: "He started it off and left it all to the others."
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Buckley, of Honeysuckle Road, Southampton, pleaded guilty to violent disorder on the day of trial at the start of November last year.
He is one of 11 men who have been jailed for the violent disorder.
Owen Eldridge was given a six-year football banning order and a 14-month prison sentence.
Charlie Morrow was sentenced to 17 months in prison and was given a six-year football banning order, while David Pilgrim, 47, was sentenced to 26 months in prison and handed an eight-year football banning order.
Bradley Scott was handed a sentence of eight months and a six-year football banning order.