In Day One of Twenty-Two Thousand, Give or Take, Matt is about to be inducted as a deputy in Mystic Falls with the other graduates. Before the ceremony, he, Caroline and Stefan make a plan to get rid of the Heretics so they wouldn't kill any other people. While Caroline distracts the heretics, Matt plants the vervain bomb in the Salvatore Boarding House and quickly goes back out. He tells Caroline it's time to go and before the timer goes off, Caroline vamp speeds with Matt. At the ceremony, Matt is inducted and the heretics quickly feed and kill off many citizens, graduates and the new sheriff, leaving Matt the only survivor. Afterwards, the heretics and the MFG make a deal that anyone who steps foot in Mystic Falls is the heretics and they leave each side alone. Matt watches the residents of the town leave and he is watched by Malcolm and Beau. He is then seen patrolling the wasteland like streets, while Damon is seen on the clock tower.

In Never Let Me Go, due to Damon and Bonnie's rivalry with the Heretics, they kidnap and take Caroline Forbes hostage. Being the Salvatore's don't own their house anymore (where Caroline is currently being held hostage inside), no one from the Mystic Falls Gang can rescue her. The Salvatore brothers then ask Bonnie to make Matt the owner of their home. In order to do so and perform a successful spell, Bonnie stops Matt's heart for 6 minutes after he is made the owner of the Salvatore Boarding House, nullifying his claim of ownership. This allows Damon and Stefan to enter the house to save Caroline.

In I Carry Your Heart With Me, while on duty and patrolling around the border of Mystic Falls, Matt catches a short bus full of tourists illegally driving in and around the border of the abandoned town. Matt lets him off with a warning and let's the tour group leave the town. Shortly afterwards, Oscar (possessed by an unknown vampire spirit) savagely feeds on and kill all of the tourists on the bus, lastly the driver.

In Mommie Dearest, after Matt found with Bonnie two dozen people compelled to gather inside Mystic Falls High School, the evening before, Matt (feeling worried), calls Caroline to see if she had news about Bonnie. He is more worried when he learns that Bonnie is with Enzo. He later goes into the Grill, with Caroline still on the phone, and trips on more stranded-compelled people on IV's. When she gets there, he tells her that the court house and the supermarket also host that kind of gathering. He points out that it’s not that clear that the Heretics are using them as blood banks because they don’t have bite marks. Instead, he thinks they are being fed before being slaughtered. That thought makes Caroline literally puke, but she doesn't want to make a big deal about it and asks him to focus on finding a way to break the compulsion. Caroline thinks that perhaps someone could Siphon the people's compulsion away and so, she bitterly texts Valerie Tulle asking her to come help them. Later, when the she joins them, the Caroline and Valerie converse and let it slip out about Caroline's pregnancy (with (Josette Laughlin's twin babies)). This surprises Matt as they work on helping out the compelled people.

In Hold Me, Thrill Me, Kiss Me, Kill Me, Caroline is writing into the journal of Elena that she is pregnant, Matt calls from his car, asking her if she wants to investigate with him about the missing people; Julian was regrouping in Mystic Falls. She turned him down and confessed that Valerie Tulle was right about her being pregnant. Surprised, he wonders how Stephen is taking it. Later, when Matt goes to the Mystic Grill, he runs into Enzo and points a gun to him while he drinks blood from the neck of a girl, ask angrily what is wrong with him. Teasing each other, Matt claims, "Nobody will ever want him in Mystic Falls, not Damon, not Lily, nobody. So what’s the point staying there?" He asked Enzo. However, Enzo shouted at him that while the Heretics are taking over the place, all Matt can do is be totally useless in trying to stop himself from drinking as he did so. This fight with the Heretics will be the death of Matt, Enzo said to him calmly, because he's overmatched and not prepared at all for what's coming. Then, getting out by the back door, Enzo was suddenly shot and fell over the ramp in the alley. Men got out from the truck and took him in the back of a prison truck. After a while, he woke up when Matt opens the back of the truck saying to Enzo (with a smug smile) to save his strength. Enzo being full of vervain, he wouldn't succeed escaping. Admitting that he can’t protect Mystic Fall by himself, Matt tells his prisoner he made some friends, who has an interest in having Enzo.

In Hell Is Other People, after hours of incantation over Damon's body in the Lockwood Mansion, Matt suggest to a totally exhausted Bonnie to take a break. A while after, when Damon finally wakes up from his repetitive day dream in the Phoenix Stone, he found himself surrounded by all his friends. Because he wants to go back to the moment he has been taken from and also because he doesn't realize he really came back, he snapped at each one of them and among them, Matt got a poker stick at the head and fell.

In Things We Lost in the Fire, Bonnie and Matt are at the border of Mystic Falls, waiting for speeding cars to get near. Matt was setting an ambush while Bonnie was trying to be positive about Damon getting better. He snorts at her, skeptical, just as she smiled to her phone, seeing his profile on a match site. But two drivers interrupt their chat and get out of their cars, immobilized by spikes on the road. Matt approaches with his gun up, but Bonnie is the first to neutralize them with her magic. While the drivers from the bunch of friends of Julian are passed out, Matt keeps kicking them and Bonnie has to stop him being Matt was about to lose it.

At the baby shower of Caroline, Matt is challenging Alaric and Tyler to a diaper contest. Alaric wins and goes talk to Caroline while the two others talk over a drink (Tyler drank only because Matt's on duty). To Tyler being fatalist about Mystic Falls fate, Matt claimed that its still their town, the one where they grew up. Disagreeing, the arrival of Nora Hildegard catches Tyler's attention and Matt’s mood immediately worsens. Later, Matt argues with Bonnie about the presence of Nora. The Heretic responsible of putting Stefan in the Phoenix Stone, and one of the murderers of his dead colleagues shouldn't be welcomed, from his point of view. With Nora stepping in, Matt felt threatened after only a few harsh words were exchanged and found himself magically choked. Not believing the aggressiveness of Nora, Bonnie begs her to stop. She frees her hold and lead her to the back of the room the baby shower was being held, both Nora and Matt glare at each other angrily.

Then Matt, in his truck, got distracted on the road and is arrested by a young, beautiful female police officer. Thinking he might be drunk, she’s not convinced at all by him trying to slip out of trouble in showing his badge. He found himself in jail for the night, having nobody to pick him up. The female officer (Penny Ares) shows sympathy for the loss of his graduated colleagues. He thanks her and they converse about how strange it seems like nobody really tried to do something about the fire that was going on. Then she brings his bag, asking him what was with all this crazy arsenal he had in the bag and his truck.

In Postcards from the Edge, still in prison, Matt looks at the female police officer doing the inventory of his bag. She seems to believe his story how he obtained all of the weird arsenal. Matt confiscated all the weapons from a illuminated group pretending to be a zombie apocalypse survivalist cult. She knows Mystic Falls as a way now to magnet people eager to live supernatural experiences. That being said, Matt is free to go, but while she gives him back his wallet, key and phone, she points out that she saw his profile on a match site and she gave him her name, Penny Ares. He smiled, but got around her and started packing his crossbow, stake gun, wooden hammer and vervain grenades. Closing the cell door behind him, she gets his attention when she mentioned a friend of hers, Doug, told her that Mystic Falls would not be burned down to the ground after all. Alarmed, he looks at her while she continued to say that her friend got a call and was informed that the risk zone would be reevaluated. Matt asked her promptly the address of Doug. When he got there, the man is dead, bloody wounded in the neck. He jumped and turn around to see Penny also armed, who followed him. From the back door, a vampire attacked them and Penny learns that she needs wooden bullets if she’s gonna patrol in Mystic Falls, hinting that Matt later teaches her about the existence of vampires.

While that was happening, Bonnie, over the body of old Rayna Cruz in a mental institution, learns from Enzo himself, that Matt managed to deliver him to a shadow organization, explaining why he was gone for so long.

Later, Matt shares a beer on his truck with Penny, all shaken up. He's supportive while she's processing the last event and what it means. She tries to get the picture of Matt: alone in Mystic Falls, without any family connection, looking to fight vampires because this town is the only constant in his life and he has to take a stand. She said to him frankly to him that he's cute and all, but mostly, he's insanely brave.

Three years from now, Matt, indifferent and deeply stricken, approaches Stefan saying that Caroline is safe, he got her out of the broadcast building and Damon was still inside. He distracted Stefan for a moment and then stabbed him quickly with a syringe full of vervain. Matt leaves him unconscious, in the parking lot and climbs the steps to the entrance to express his message to a camera turned on, "All right I did it, he's out. I'll never see you again right?" A female voice thanks him and he leaves. Then the glass shows a reflection of Damon's improvised cell, which is also showing us the grin of Rayna Cruz.

In Moonlight on the Bayou, in the deputy office, Matt is on the phone with Caroline wondering where Rayna Cruz is. Valerie comes into the office and assures him that she can help with that. She give him a map with written-in dots on where Stefan is on the road (to New Orleans), echoing to what Caroline said, "Rayna Cruz is where Stefan is." Matt paused for a moment and started to complain about the irony of him being in need of her help beside the fact that she killed all of the sheriff department. After Valerie's persistence, he seems to be sensible to the fact that Valerie truly has been helping his friends (Caroline first of all and now Stefan). He finally agrees to keep her posted if any reports come up of Rayna Cruz "stilling a car or something."

In I Would for You, Penny and Matt are amusing themselves with a scenario they have been playing along with on how to trap Julian's vampires for a couple of days. They are surprised by vampires from Julian's army however, Krystal and four more of them. Shortly after, Julian's vampires fall to the ground, stabbed by Rayna Cruz, who asks Matt if he knows a vampire named Stefan Salvatore. Later, Matt and Penny on her side, she interrogates a vampire at the Grill. She wants to know where Stefan is. Matt covers for him and teams up with Damon when he barges in. Matt shoots Rayna in front of an uncomprehensive Penny. Then, alone at the Grill, she asked him why he chose to help Damon. Skeptical about the fact that they're are some good vampires, she points out that all Matt has been talking about lately was his hate for that species. She questions his motives and she accuses him of being guilty as the vampires in what the town has become because he never took a real stand, he is hurt by this and becomes very thoughtful about this. In the evening, Matt let himself in the Salvatore mansion to talk to a devastated Stefan. Firmly and calmly, he says that he has enough of being at the mercy of vampires. Despite all his efforts in Mystic Falls, humans are no match for them, but "it stops now." He continues (even to Stefan) to stand up as he felt threatened because "vampires need to leave town," Matt says. And he takes a USB key out of his pocket containing the footage of Damon ripping the heart of that interrogated vampire at the Grill. He plans to use it to expose the existence of vampires if they don't leave for good. It has to be done for the protection of the town, already torn apart. Not happy that Matt blackmailed Stefan, his friend, makes his way to the main door giving him and Damon until the end of the day to leave Mystic Falls.

In Days of Future Past, Matt is seen walking to Penny Ares' grave with tears in his eyes. Stefan Salvatore had an involvement (unknown why yet) with Penny's death. It is also revealed that Matt is the one who helped Rayna Cruz escape her imprisonment from the Armory. At this point, Matt has turned against all vampires, especially his old friends and Stefan Salvatore.

In I Went to the Woods, Matt is desperate to find Stefan when his plan to use Rayna Cruz to hunt Stefan fails. Although Matt hates the Heretics, he asks Valerie Tulle for assistance on helping him search for Stefan. Matt finally gets to Stefan.

In Kill 'Em All, Matt spends most of this episode trying to get Stefan to tell him what's exactly happened to Penny and her death. Stefan reveals that he compelled Matt to forget that it was Matt himself who shot Penny to death, not Stefan. Matt breaks down, but shortly says that he still blames Stefan for being around Mystic Falls when Penny was shot to death.

In Requiem for a Dream, Matt is informed by one of his inferior officers that there are supposed squatters taking up residence in the abandoned-Salvatore Boarding House. Matt later finds Enzo solemnly drinking bourbon and Enzo tells him that Bonnie gave in to her Supernatural Huntress side. Matt later gets in touch with Bonnie and he allies himself with her. Matt later betrays Bonnie by shooting her with vervain darts and she falls unconscious. Damon thanks Matt for saving his life and assists in helping Bonnie into Matt's pickup truck. Matt sadly talks about blaming himself and Stefan for Penny's death as they hoist Bonnie's unconscious body into his truck. Matt is later seen driving and Bonnie suddenly awakens and suffocates Matt until he is unconscious. Bonnie takes over Matt's truck and speeds back to Mystic Falls to try and kill Damon once again

In Gods and Monsters, Matt is abducted by Bonnie and they are driving together to try and catch up to Bonnie's vampire victims. Matt tries to help Bonnie see through the Supernatural Huntress-side of her and helps her to steer her away from being able to catch up to her vampire-targets. Matt eventually crashes them both into a forest area on the side of the highway. Bonnie apologizes to Matt and leaves him to hunt down the rest of their friends. During this time alone, Matt hallucinates seeing his dead fiancée and he apologizes for killing her. Penny tells him to love his life away from Mystic Falls and Matt does so as a police unit finally finds him and helps him out of the crash. This starts the phase of Matt moving on from Mystic Falls and the dangerous, vampire hunting-lifestyle.