When Nora Buchanan gave birth to Matthew in 1999, she believed he was the product of an affair she had with hotshot attorney Sam Rappaport while she was married to Police Commissioner Bo Buchanan. Matthew was almost born too early, and Sam carried Nora through the snowstorm to the hospital. He was delivered and after a scare when he had a seizure, he was brought home happy and healthy. Matthew was diagnosed with a rare muscle condition in late 2001 by Troy MacIver, who cured him with a risky medicine still under experimentation, earning the adoration of Matthew for his "Dr. Troy." In late 2003, Matthew and the rest of his family were shocked to learn that he was actually the son of Nora's now former husband Bo Buchanan. Although Matthew began forming a relationship with his newfound father, even after Sam's death, he made it clear that he wanted to remain Matthew Rappaport, in honor of the man he had originally thought was his father. Shortly after his mother's marriage to Daniel Colson fell apart, though, Matthew was thrilled to officially become Matthew Buchanan, which was a wonderful Father's Day gift for Bo.

In the fall of 2008, Matthew entered high school as a freshman and quickly began to feel the familiar pressures of fitting in. Being the son of the town's district attorney and police commissioner didn't make things any easier for Matthew. He liked a girl at school named Becca, but she wouldn't give him the time of day. Matthew decided that portraying himself as a rebel would win him the girl and help him fit in with other kids, so he liked to his friends about doing drugs and even bought a joint to prove he wasn't a goody two-shoes. When Nora found the joint in Matthew's backpack by accident, she went to Bo and told him her fear that Matthew was doing drugs. Nora and Bo confronted Matthew, who at first lied about the joint but then said the joint was his and that he didn't think it was a big deal. Bo was very angry and felt he couldn't understand why Matthew was acting up. Matthew later discovered that his friend Cole, a high school senior who was living with him at the Buchanan mansion, was doing drugs. Matthew confronted Cole, but Cole wouldn't listen to reason and continued to take drugs to escape his life. Cole later took the joint from Matthew and smoked it outside the front door of the house, leaving the remainder of the joint for Bo and Nora to find. When Bo and Nora went to the school to confront their son, Matthew liked to impress his schoolmates and told his parents he smoked it. Cole overheard, but didn't say anything. Bo said he was going to send Matthew to military school, over Nora's objections, but he later reconsidered after having a heart-to-heart with Matthew, who admitted he had a crush on a girl. Matthew made a friend in a feisty girl named Destiny, who appeared to have a crush on Matthew although Matthew didn't realize it.

At a school dance in March 2009, Matthew asked Becca to dance and Becca agreed on a dare. Matthew was then humiliated when another kid named Justin had the DJ dedicate the song to Becca in Matthew's name and Becca rejected him. Everyone except Destiny laughed at him, and Matthew raced out of the school and jumped into the passenger seat of Cole's car. Cole, who had just taken a handful of pills after seeing his ex-girlfriend Starr making out with her teacher, told Matthew to get out of the car but Matthew refused. Cole zoned out while driving and swerved off the road to avoid hitting an oncoming car. The car flipped over, and Matthew was thrown from the car. Bo found Matthew lying on the side of the road and had him rushed to the hospital, where Dr. Michael McBain performed tests and determined that Matthew couldn't feel his legs. Later tests confirmed that Matthew was paralyzed from the waist down and would probably never walk again. Bo and Nora broke the news to Matthew, who felt that his life was over. Matthew also blamed himself for getting in the car with Cole and not wearing his seatbelt. Destiny visited Matthew at the hospital and offered him moral support. With his parents' encouragement, Matthew stopped blaming himself and accepted that his life wasn't over - although it would be forever changed.

Matthew was ridiculed by Justin and Becca when he returned to school, but they changed their tune when Destiny scared them into thinking that they could be arrested for contributing to his accident. Unfortunately, it backfired on Destiny when Becca showed up at Matthew's house and gave Matthew a kiss. Matthew was grateful when his older sister, Rachel, returned to town from Chicago to help him out following his accident. Rachel encouraged Matthew to attend the prom, where Matthew was introduced to the Pussycat Dolls. Matthew continued to get closer to Destiny, although he seemed oblivious to the fact that Destiny liked him as more than a friend.

Matthew was stunned when Clint announced, in front of Nora and Bo, that he had found a doctor who said he could help Matthew walk again. The doctor turned out to be Destiny's older brother Greg Evans. After reviewing Matthew's tests, Dr. Evans told Nora, Bo and Matthew that he could help Matthew walk again. But when Nora learned the surgery could be life threatening, she told an angry Matthew that she refused to let him have the surgery. Matthew shocked his parents when he said he would rather be dead than stuck in a wheelchair for the rest of his life. With Destiny's urging, Matthew hired attorney Téa Delgado to take his parents to court and force them to consent to the surgery. When Matthew spotted his parents kissing on the night before Nora was to marry his Uncle Clint, Matthew attempted to blackmail Nora and Bo into allowing him to have the surgery in exchange for him not telling Clint about the kiss. Nora and Bo called Matthew's bluff, but Matthew decided not to tell Clint because he knew it would hurt Clint, who had been the one to find Dr. Evans in the first place. On the day of his mom's wedding, Matthew leaned in to kiss Destiny but was interrupted by Téa.

Matthew scored a victory in court, but then Greg refused to perform the surgery because his brother Shaun had fallen into a coma after Greg operated on him. Undeterred, Matthew found a doctor in Seattle who would do the surgery and told his parents he was going there. Nora and Bo offered to fly Matthew there on the Buchanan's private jet, but while en route Matthew learned they were really flying to London and he was being enrolled at a boarding school there. Matthew quickly hatched an escape plan with a fellow student, Danielle Rayburn, not realizing that Danielle was the daughter of his attorney Téa and Todd Manning. Destiny showed up in London to see Matthew, just as he was leaving with Danielle. With Destiny's help, Matthew and Danielle escaped the school and flew to Seattle, where Matthew underwent his surgery. There was a brief scare in the operating room, but Greg Evans assisted and the surgery was deemed a success. On Thanksgiving Day 2009, with his parents and the Evans family by his side in the hospital room, Matthew started to regain feeling in his legs. Matthew was shocked when Danielle showed up at the hospital, looking for a place to hide out from her mother. When Ross showed up and took Dani at gunpoint, Matthew was worried sick and refused to return to Llanview until he knew Danielle was okay.

Danielle emerged from the incident unscathed, but Ross was shot by Todd fell off a bridge to his apparent death. Danielle was furious at Téa and Todd and vowed never to forgive Todd for killing her father. Back in Llanview, Danielle saw Matthew's father Bo putting his gun in a locked safe and later stole the gun. She held Todd at gunpoint on New Year's Eve and threatened to shoot him before Blair appeared and talked her out of it. Téa decided to take Dani back to Tahiti. Dani said goodbye to Matthew, and they kissed. In Tahiti, Dani discovered Ross was actually alive and learned that Todd was her biological father. After returning to Llanview, Danielle researched Todd's past on the internet and learned about all of his crimes. Matthew tried to console her and took her to meet her sister, Starr. Starr said it would take time but maybe she would one day get to know Todd like she does, and she invited Dani to stay with her at Cole and Markko's apartment. Matthew confided in Destiny that he and Danielle had kissed and that he liked her as more than a friend. Matthew and Danielle began dating, and eventually Destiny became a good friend to them both.

Matthew stood by his mom after his father got shot in the line of duty, but Bo pulled through and then proposed to Nora. Matthew was excited to hear the news, and agreed to be best man at the wedding.

When the school began casting for a musical centered on Starr and Cole's lives, Destiny and Matthew agreed to try out. Danielle came along to watch and ended up trying out as well, stunning everyone with her lovely voice. Dani was cast in the lead role of Starr, while Destiny and Matthew were cast as second bananas Langston and Markko. Matthew was jealous of the new kid in town, Nate, who was cast as Cole and had to spend a lot of time rehearsing with Danielle. During rehearsal one day, Destiny confided in Matthew that she had seen Langston making out with Robert Ford, a teaching assistant at Llanview University. They both agreed to keep quiet, but neither realized that their conversation was being recorded on a camera Markko has accidentally left on. Matthew and the rest of the cast were shocked when Cole stormed into the gym and beat up Todd, nearly killing him, after believing that Todd had pushed Marty down the stairs and killed her baby. Matthew asked Danielle to be his prom date and she accepted. Matthew confronted Danielle after sensing from Nate that something had occurred between them, and Dani admitted she had kissed Nate but told Matthew it meant nothing. Matthew warned Nate to stay away from Dani. After taking Dani back to her mom's after prom, Matthew told Dani that he loved her. Dani couldn't say it back, and Destiny later told Matthew he came on too strong.

On the day Matthew's parents remarried, Danielle told Matthew she only wanted to be friends with him. Matthew figured out that she was really interested in Nate, and he set out to punish Nate for taking Dani away from him. After learning that Nate had come upon $50,000 in cash, Matthew ratted out Nate to a thug named Bull who was trying to track down the stolen loot. Nate ended up getting kidnapped and held for ransom, but he escaped with Dani's help when Todd showed up and shot Bull dead. Matthew blamed himself for putting Nate and Dani in danger, but David assured Matthew he had done nothing wrong.

While Matthew's parents were on their honeymoon, David hired hookers and encouraged Matthew to lose his virginity to one of them so he could forget about Dani. Although Matthew spent the night with his call girl, he never slept with her. Matthew still pined for Dani, and he let out his frustration on Nate whenever he could. Matthew treated Nate as a common servant while visiting the country club, where Nate was working part-time during the summer. After learning that Dani's mother Téa was dying, Matthew apologized to Dani for his horrible behavior and told her he would always be there for her.

Still, Matthew harbored deep-seated anger toward Nate. When he learned Bo had hired Nate's mother Inez as his new assistant, Matthew was furious at his father and ordered him to fire Inez. But Bo told Matthew everyone deserved a job, despite what he may think. Matthew turned Bo's words against him when Clint offered to show Matthew the ropes at Buchanan Enterprises. Clint told Matthew that he was impressed with how he had handled himself with Nate, saying it showed a cunning business sense, and that Asa had wanted him to eventually run the company. Matthew pressured Bo into allowing him to intern at BE after school. Matthew proved his loyalty to the family almost immediately, when he caught Rex trying to steal files from Clint's office and alerted security.

Matthew proved himself a valuable asset to BE, so Clint gave him a raise and gave him additional duties. But Matthew also grew curious about Clint's private business dealings. He learned Clint had ordered one of the BE associates to manufacture a key card for the Llanview Hospital DNA lab and later realized Clint had undergone testing at that lab to prove he wasn't Rex Balsom's biological father. Matthew discovered Dorian Lord locked inside Clint's office after she was rifling through his desk. Dorian paid him to let her go but then Matthew went through the desk and discovered a heart-shaped necklace that Clint later explained was the key to the Buchanan fortune. When Matthew questioned why Clint was being so nice to Inez Salinger and her children, Clint recalled one of Asa's favorite sayings: Keep your friends close, but your enemies closer. Matthew questioned why that didn't apply to Rex, and Clint had no good answer.

Matthew stunned Clint by revealing that he had figured out that Clint was Rex's father. Clint admitted that it was true but told Matthew that Rex was a con man not worth the Buchanan name. Clint then informed Matthew that Inez had left him and that she and Bo had been having an affair for some time. Matthew didn't want to believe it, but he caught his father and Inez kissing at her apartment and realized it was true. In a rage, Matthew called Dani and told her to tell Nate that his mother was a whore and home wrecker. Matthew then nearly hit an oncoming car while fumbling with his phone. The next day at school, Matthew told Nate that Inez and Bo were having an affair. After Nora chided Matthew for having an attitude with his father, Matthew revealed that he had seen Bo and Inez kissing and knew they were having an affair. Nora and Bo separated briefly but later reunited, explaining to Matthew that it was a misunderstanding. They forbid Matthew from interning at Buchanan Enterprises but refused to explain why. An angry Matthew told Clint everything and said he still wanted to keep his job. He returned and declared to Nora and Bo that he had quit. He later told Destiny the same thing. Destiny thanked Matthew for not pressuring her to reunite with her own parents, who had lied to her about upbringing, and they engaged in a kiss.

Matthew seemed distracted in the weeks following kissing Destiny, but he told Destiny it had nothing to do with her. He was concerned that his parents were going after Clint for murdering Eddie, insisting that his uncle was innocent despite everything else he had done. Matthew showed up in court in April 2011 as Clint was about to be arraigned for Eddie's murder and was relieved when the charges were dropped. He then realized that his parents knew the truth: Matthew had murdered Eddie Ford in the heat of the moment after running into Eddie and realizing that he had been with Nora, who was nowhere to be found. After shooting Eddie with his own gun, Matthew threw up and called Clint, who got rid of any evidence implicating Matthew.

Matthew told Nora that he would turn himself in, but Nora and Bo delayed turning in Matthew as they tried to figure out a way to keep him out of jail. Meanwhile, Destiny told Matthew that TV reporter Blanca Morales had questioned her about the murder and was convinced that Matthew was guilty. Matthew told a stunned Destiny that it was true. Matthew and Destiny kissed, and then Matthew took Destiny into his bedroom and they had sex for the first time in May 2011. Destiny figured it was a one-time thing, but Matthew told Destiny that it meant more to him than that.

Nora and Bo told Matthew that Blanca was threatening to expose Matthew as the killer, and Matthew offered to turn himself in. But Bo and Nora urged him to wait, hoping they could convince Blanca to back down, and told Matthew to stay in the apartment. Matthew answered a pounding knock on the front door and Nate Salinger immediately punched Matthew in the face, accusing him of killing Nate's father. Matthew fell to the ground, hitting the back of his head on an end table in the process, although he quickly got up. Nate demanded that Matthew admit what he had done, and Matthew came clean. Nate promised to go to the cops unless Matthew turned himself in. Shortly thereafter, Destiny showed up and told Matthew that Clint had just confessed to Eddie's murder on live television from his hospital room, where he was recovering from a heart attack. Matthew complained of a headache and Destiny got him some pills before leaving. When Nora and Bo arrived, Matthew was about to tell them about his visit from Nate when he fell to the floor, unconscious. Bo and Nora rushed Matthew to the hospital, where doctors detected a small bump on his head and decided to run some tests. Matthew awoke but was confused, thinking he had just been in the car accident with Cole and was paralyzed.

The tests revealed Matthew had suffered a serious head trauma and needed immediate surgery. Matthew made it through the surgery but had only minimal brain activity. The doctors urged Bo and Nora to take their son off life support and allow his heart to be donated to Clint, whose heart was failing, but Nora refused to even consider such an action. While Destiny was visiting, Matthew opened his eyes and squeezed Nora's hand when she asked him to, giving everyone hope that he would be alright. Matthew said David's name when he visited, and later acknowledged Bo's presence. But when Bo tried to question Matthew about the accident, all Matthew could get out was the word "Eddie" before he began having a seizure.

Weeks later, Matthew suffered another seizure while trying to tell his mother that Nate had punched him. The doctors told Nora and Bo that Matthew needed to be transferred to a rehabilitation center in Philadelphia where he could be looked after properly. Nora and Bo reluctantly agreed. Bo and Nora grew frustrated that Matthew showed no progress at the rehabilitation facility. But when Nora overheard Destiny tell Matthew that she was pregnant, Nora pleaded with Destiny to keep the child because it could be her only tie to Matthew. Destiny reversed her decision to have an abortion and decided to keep the baby, sparking a rift between Nora and Destiny's mother.

Bo and Nora were visiting Matthew on Thanksgiving Day in November 2011 when Matthew suddenly flatlined. It seemed that Matthew was dead, but the doctors managed to revive him and Matthew opened his eyes for the first time in months. Destiny came to visit and Matthew realized that she was pregnant, but he didn't realize the baby was his until Destiny told him. When Matthew learned that Nora had pressured Destiny to keep the baby, he was livid. Matthew had lost months of his life and didn't want to be saddled down with a new baby. He told a devastated Destiny that he would support her and the baby but didn't want to be a father and didn't want to be tied down to her. David tried to talk some sense into Matthew and revealed that he had also gotten a girl pregnant while he was in high school. But David got interrupted before he could tell Matthew what happened to the child. David told Matthew he needed to "Buke Up" and take responsibility for the baby he helped create.

In January 2012, Matthew showed up at the Buchanan mansion and was stunned to learn that Destiny had gone into labor and was about to deliver their child. Matthew raced to Destiny's side and helped her deliver a healthy baby boy, which they decided to name Drew after Matthew's late older brother. However, after Drew's birth, Matthew distanced himself from Destiny and their child. He insisted that he had not chosen to be a father despite his family's disappointment in his decision.

Although Matthew did not make time for his son, he did find time to be online and he started chatting with a woman named Michelle. His roommates, Jeffrey and Dani, were surprised by the amount of time he spent online with someone he had never met. Matthew feared that Michelle did not exist after he traveled to her supposed home and discovered that she did not live there. Jeffrey tracked Michelle down and discovered that she lived in Llanview and arranged for Matthew and Michelle to meet. Despite her initial dishonesty, Matthew forgave Michelle.

Matthew rapidly developed serious feelings for Michelle and they became lovers. Dani and Jeffrey also spent a bit of time with Michelle and observed some discrepancies in her stories. Matthew was warned by his roommates to proceed with caution with Michelle but their warnings led Matthew to protect Michelle from his friends. Matthew was also forced to reveal to Michelle that he had a son after Drew was briefly hospitalized with a high fever. She took the news well and Michelle agreed to be Matthew's date to the "Man of the Year" gala but he worried about Michelle after she had a verbal altercation with Dani. Matthew took Michelle's side against Dani, unaware the Michelle had intentionally stirred up the trouble to cause a rift between Matthew and Dani.