When the school year started, Elena knew Matt was still upset about their break-up. During history class, Matt noticed the new guy, Stefan Salvatore, staring at Elena, and even saw Bonnie Bennett text Elena about it. Elena brought Stefan to the Mystic Grill and introduced him to Bonnie, Caroline Forbes and Matt. During the Back to School party, Matt told Elena he still believed in them and though she broke up with him because she needed some time to be alone, she didn't seem alone, as she was hanging out with Stefan. Later, Elena and her brother Jeremy found Matt's sister Vicki in the woods, who was attacked by what they thought was a wild animal, but was really Damon Salvatore.

Tyler Lockwood, Matt's friend tried to embarrass Stefan in front of Elena to show her she "chose wrong", by attempting to hit him in the back of the head with a football, but was shocked and slightly humiliated when Stefan turned around in a split second and caught it before it hit him, surprising everyone and impressing Elena. Elena encouraged Stefan to join the football team, and their coach and history teacher William Tanner eventually permitted. Everyone was impressed with how good he was, causing Tyler to try to get Matt to tackle Stefan and embarrass him again for showing them up. Stefan overheard them talking and let them tackle him roughly as a way to make themselves feel better.

Bonnie told Matt to stop pining over Elena, as they saw she was happy with Stefan. He later found out that Elena and Stefan broke up, but saw they were still hanging out together. Eventually, Stefan and Elena got back together and Matt started dating Caroline. Caroline, wanting to show Matt that Elena was happy with Stefan, set up a double-date, but when Matt and Elena started reminiscing their childhood memories, Caroline became upset, although Stefan enjoyed the conversation, and understood that she and Matt have history. The date started to "improve" has the night drew on but it was cut short when the four entered the Salvatore Boarding House to find Matt's mother Kelly and Stefan's brother Damon Salvatore making out, enraging Matt.

While trying to get to a birthday party, Caroline's car broke down in the middle of a thunderstorm. She couldn't find cell service, and got out of the car in the downpour to try to find a place with a signal so she could call for help. She slipped and fell down a small mudslide; she slid down the hill and grabs for a plant to hold onto, accidentally grabbing the wrist of a dead body that was found to be Vicki Donovan, much to her horror. Caroline and her mother, Sheriff Forbes delivered the grave news to Vicki's family. Matt, grieving his sister's death, told Caroline he wanted to be alone, before Elena shows up at his house. When Matt sees Elena come in, they run to each other and hug, upsetting Caroline.

Matt was unable to escort Caroline to the Founder's Day Celebration, due to work. Ironically, Elena wasn't escorted by her boyfriend either. 

While both Elena and Matt were helping prepare for the Masquerade Ball, Matt asks Elena about Caroline, who he had just broken up with, and tells her he thinks she is seeing someone else. She tells him that Caroline isn't dating anyone, and tells him to 'just give it time', in an attempt to hide the fact that Caroline is now a vampire.

Matt helps Elena bring home from the hospital after Jenna nearly died after stabbing herself in the stomach (due to being compelled by Katherine Pierce.) Later, Elena and Matt discuss their lives, and Matt asks Elena if she's going to the Masquerade Ball. Elena tells him that she isn't, since she and Stefan are broken up, and Matt replies that he's going because there is something he needs to do, although he doesn't go into detail. He assures her that he's always here for her, and leaves for the ball.

During Elena, Bonnie, Caroline and Jenna's girl's night, they go to the Mystic Grill to see a band perform, and Elena walks into the ladies' restroom to find Matt and Caroline making out, and Elena tells them she's happy that they've made up. The power goes out, and it is revealed that Jonas Martin is there to take Elena to Klaus to trade for his daughter, and the gang try to protect Elena. Caroline attacks Jonas, who hits her with a mystical brain aneurysm spell, causing her to fall onto the ground in pain. When Matt sees Caroline crying, he runs up to Jonas to protect Caroline. Jonas stabs Matt in the neck with a broken beer bottle and leaves, leaving Caroline to help Matt. She almost feeds on him when she smells the blood, but eventually controls herself and feeds him her blood to heal him, and takes him back to her house.

After Matt found out about vampires, and that Caroline is one, he disappears, freaking out because he thought Vicki was just tripping on drugs when she told him that she was hurt by a vampire. Elena tells Caroline that Matt is not one to run away, and offers to help her find him, but is ultimately unable to because she is kidnapped by Katherine and Isobel. Matt has Caroline tell him everything about vampires and the supernatural, and then gets overwhelmed and asks her to compel him to forget. She does, and it is later revealed that he is working with Caroline's mother, Sheriff Forbes, and had taken vervain and only pretended to be compelled. 

Matt attends Elena 18th birthday party, in which Elena spots him getting smoking marijuana with Jeremy. Caroline blames herself for Matt's drug use, but Elena assures her that Matt is just sad that he's not with her anymore.

During Senior Prank Night Matt and Elena help the other by setting up pranks around the school. When Klaus threatens to kill Tyler (by attempting to turn him into a hybrid, even though he had had no success in creating them so far) and Elena (who he believes is the reason why he can't turn hybrids), Matt kills himself by drowning himself in the swimming pool, and has Bonnie revive him with CPR so that he could contact his sister Vicki on the Other Side and find a solution to help Elena. It is eventually learned that Elena (the doppelgänger)'s blood is what creates a successful hybrid, and Tyler and Elena's lives were spared.

In Homecoming, Matt and Elena plan to go to the Homecoming Dance together when his date, Rebekah, is neutralized by a dagger, but that didn't end up happening because Katherine took Elena's place in order to keep Elena out of harms way when they tried to take out Klaus.

In Our Town, Matt and Elena plan Caroline's birthday party. However, when Caroline admits her disappointment that she's sad to be stuck at age 17 forever, Elena, Bonnie and Matt decide that what Caroline needs is a funeral, so she can mourn her human life, and move on with her new one. When Caroline doesn't return from her walk with Tyler, Matt and Elena start looking for her. They find her, hallucinating due to being bitten by Tyler, who was under Klaus' sire bond. Klaus eventually heals her with his blood. The next day, Elena and Matt meet at Wickery Bridge; she tells Matt about all that has happened since she nearly died in the car accident that killed her parents, and that, in a way, she feels like she let her former self down. Matt tells her that she's not that girl anymore, and tells her that it's okay for her to let that girl go and move on. Matt takes a handful of dandelions and throws them in the river as a symbol of moving on to her new life.

In Bringing Out The Dead, Matt shows up to comfort Caroline, after her dad's death. Elena watches and smiles at her friends comforting each other. Matt walks Elena home, where they arrive to find the power out. The two grab knives off the table and search the house, where they find Alaric in a hallway, stabbed, bleeding, and near-death. Elena has no other choice but to kill him, so that he can be revived through his ring, as they don't know if the assailant was supernatural, but they do know that Elena is supernatural, as the doppelganger. Matt watches in horror as Elena stabs him again, killing him. After Alaric dies, they move him upstairs, where Elena asks Matt to stay with her until Alaric wakes up, confessing that she can't lose anyone else in her life. Matt assures her he'll stay, and they wait around Alaric's body.

In The Departed, Matt and Jeremy struggle with what to do to protect Elena from the Original Vampires and the-newly-turned enhanced Original vampire, Alaric, who is on a mission to kill all the vampires, and whose life is tied to Elena's life. He decides to drug Elena's tea so she will go to sleep, and then puts her in his truck and drives to take her out of town. They're still on the road when they get news that Alaric staked Klaus with the indestructible white oak stake, which means that Tyler, Caroline, Stefan and Damon will die, as a part of his bloodline. She screams that they have to turn back, but Matt says that Damon is 100 miles away. They can keep driving to him, or they can turn back to go to Stefan and the rest of the gang. Elena eventually chooses the latter, and calls Damon to say goodbye. After hearing about Klaus' death, Rebekah calls Stefan and tells them their deal is off, and that she's tired of running, and her only choice is to kill Elena so that Alaric will die and won't be able to kill her. Matt is handing Elena his cellphone when Elena sees someone in the road. She screams and Matt swerves the car, flipping off the Wickery Bridge and into the river below. Stefan runs to rescue Elena, and she gestures to save Matt first. While Stefan is taking Matt back to land, Elena drowns. Damon returns to Mystic Falls after Alaric dies, and runs to the hospital to see Elena, where Meredith Fell explains to him that Elena died with vampire blood in her system, from when Meredith treated her injuries from the day before, which were more extensive than anyone realized. 

Matt: I still believe in us.

-- Pilot.

Elena: Still wanna be an astronaut?

Matt: I can’t believe you remember that.

-- The Turning Point.

Elena: Well, we were wasted; there was the first time I ever got drunk. I blame Matt.

Matt: Her parents got seats at the next booth.

Elena: And Matt and I were pretended that I was choking so we can get away.

Matt: Except that her dad was a doctor so he jumped out to save her.

-- There Goes the Neighborhood.

Elena: No, it’s great that you are enjoying yourself. Thanks for making me dance.

Matt: Hey, it’s normal.

-- Under Control.

Matt: So, where’s Caroline? This is like her thing. I can’t believe she’s not here.

Elena: She has something else to do.

Matt: Is she seeing someone?

Elena: Matt, come on. No, she’s not.

-- Plan B.

Elena: You look good in a suit.

Matt: You and Stefan are working it out.

Elena: I don't think so, Matt. There's so much about me and Stefan that'll never work.

Matt: You know I'm here for you always.

-- Masquerade.

Elena: I wish I did, but he wasn't really one to run (about Matt).

--Know Thy Enemy

Matt: Hey guys. (big smile)

Elena: Matt, hey! (He kisses her on the cheek) oh..

Matt: Happy Birthday.

Elena: Thank You. Hmmm...

-- The Birthday.

Matt: You're not that girl anymore. It's okay if you want to let her go.

Elena: Is it? Cause I feel like I disappointed her a little like, if I disappointed them. My parents.

Matt: For my too sense, as a guy who knew that girl, you're doing better than you think. Here lies Elena Gilbert. A girl-friend, and an amazing friend.

--Our Town

Matt: Are we running a marathon.

Elena: If you can't keep up.

Matt: Elena you can't out run your problems. Looks like you're going to try.

--1912