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Madison was a classmate of Jamie Scott during his time at St. James Day School. Intelligent and athletic, Jamie developed a crush on Madison while the two were in elementary school.

Jamie's feelings for Madison were made apparent in the eigth season when he purposely lost to her in their school spelling bee. Later, Madison Madison joined a little league baseball team coached by Julian Baker, Clay Evans, and Nathan Scott, where she was teammates with Jamie. While it was initially unknown whether Madison returned Jamie's affections, she seemed to reciprocate his feelings when he presented her with shoelaces on Valentine's Day. Jamie wore one pair of the shoelaces while Madison wore the other. However, when their classmate Chuck Scolnik made fun of Jamie's shoelace, he stopped wearing it, which noticeably hurt Madison's feelings, as she returned her shoelace back to Jamie.

When Madison began hanging out with another boy instead of Jamie, his aunt Quinn James encouraged him to tell Madison how he felt. When he did so, he returned the shoelace he had gifted to Madison back to her and they resumed wearing their pair of shoelaces. With matching grins, it was evident Madison and Jamie had acknowledged their crushes on the other.

Character arc[]

Season 6[]

Season 7[]

Season 8[]

Madison and Jamie both competed in a school spelling bee. Jamie spelled a word wrong, then Madison then spelled it correctly. However, he did it purposely to let Madison win. They were both driven home by their teacher, Lauren, along with Chuck Scolnik. There was a large storm going on and the car flipped. Jamie's godmother, Brooke Davis, was driving by and saw them. Chuck was bleeding from his head and Lauren was passed out. Brooke managed to get Madison, Chuck, and Lauren into her car and Lauren drove for help. Jamie was trapped in the car and another driver hit it, which sent him and Brooke into the water, where they nearly drowned.  Madison also participated in the Tree Hill little league team, the Sharks.  In their first game, Madison did not get a hit her first few at bats, but on her last, she got a single. On valentines day, Jamie gave her shoelaces, and Madison put one on, and Jamie put on the other. Jamie took his off and so did Madison. Madison is seen walking at the end of a school day with a boy other than Jamie. Madison gave her shoe lace back so Jamie gave her another, but Madison that back too. Quinn told Jamie to tell her how he felt (that he still had feelings) and he did. He gave her the shoe lace one more time. Jamie then saw the other shoe lace in his locker and saw Madison wearing the other, then they grinned at each other.

Season 9[]

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