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Madison Landry was a classmate and girlfriend of Jamie Scott who was also on his little league basketball team coached by Antwon Taylor as well as his little League baseball team coached by Julian Baker, Nathan Scott, and Clay Evans. Jamie also bought Madison shoelaces as a Valentine's Day gift where Madison and Jamie wore one pair of shoe laces on one shoe. One day, Chuck teased Jamie about his shoelaces so he stopped wearing them. Madison noticed and stopped wearing hers and then Jamie saw her at the movies with a different boy.
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 legue 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.