A/N Disclaimer I do not own Harry Potter or associated characters. That pleasure belongs to JK Rowling and Warner Bros.
Ron Weasley is a Chudley Cannons' supporter. As soon as he saw the bright orange jerseys and the fact that they kept fighting even when losing 500 to 20 he was hooked. That's what Ron's life was like. He could never win against his brothers but once in a while he earned 20 points.
The Chudley Cannon supporters are the true fans. They are the die hard supporters the ones who never stop believing in the impossible, willing to stand out from the crowd in order to support their team. Every time they don the orange jersey with the double C's they are saying "I believe that unsurmountable odds can be beaten, that the little team can beat the big one." They may be unrepresented and unnoticed in professional circles but they are the fighters in the league. Sure they've never won the league but they're the only team who have always competed in it. They are the stayers, the tryers. The Cannon's never give in and neither do their fans.
Ron is a die hard Cannon's supporter. That's why he is the perfect friend for Harry Potter: The Chosen One; The Boy Who Lived. A child against a Dark Lord, a Muggle-raised wizard with no knowledge of magic before the age of 11. It was the Cannons against the Holyhead Harpies. it was Lithuania versus Ireland. Being a Cannon's supporter means you believe in the underdog, you know that one day David will beat Goliath and the day it happens will be a day of celebration. Ron has always believed that Harry could end Voldemort, he may have left him out in the cold a few time but deep down he has always known Harry will be the one to defeat him.
Everyone else saw the weak scrawny kid who didnt know a single spell when he arrived, who struggled to learn spells, who didn't get top marks in class but Ron? He saw something different. He saw the child who arrived knowing nothing but managed to work hard and achieve something. So what if he didn't get O's in every subject if there was something he thought he should know he'd learn it through practice and stubborness. Harry Potter is an impossible bet, a 1 000 000-1 chance that he can defeat Voldemort. A lost cause.
Ron likes lost causes, he supports them.
He still believes the Cannons will win the league.