He was sent to Degrassi Community School as a student teacher. He was assigned to the Media Immersion class, where he met Paige Michalchuk. After a period of time, she finally convinces him to enter a secret relationship with her. When Manny Santos unveils their relationship to everyone, Matt is fired and sent to Nunavut.
In Bark at the Moon, Matt and Paige argue about their relationship. He tries to kiss her outside of the dance, but Manny accidentally sees, and they both flee the scene. Outside of school, Paige and Matt continue arguing, but come to an agreement that they want to see each other, ending up kissing. During class, Matt would give Paige notes, making Hazel, Paige's best friend, become suspicious about the two of them being together, which she later confronts Paige about. After a catfight between Paige and Manny, Manny reveals the two's secret relationship in front of everyone and Mrs. Hatzilakos. Matt tells her that Paige was obsessed with him and stalked him. Though after many fights, Paige and Matt continue to see each other.
Matt returns in Death of a Disco Dancer after being sent to Nunavut. Paige gets him a gift, and he breaks up with her, finding the two of them to be too different from each other. Matt leaves for Kingston this time, and for good.
- He gives Chris Sharpe a lesson on respect in Modern Love, after Chris insults Emma twice. However, the lesson is shown offscreen.
- Matt is the first teacher to be in a relationship with a student, the second was Mick, the third was Ms. Oh, and the fourth was Grant.
- He is the first Matt in the Degrassi Franchise. The second is Matt Barnes.
- Matt is one of the six teachers to be crushed on by a student. The other five were Mr. Colby, Daphne Hatzilakos, Archie "Snake" Simpson, Winnie Oh, and Grant Yates.
- Mr Oleander was the second of six teachers in DTNG who were rumoured to have sexually abused/harassed a student, he was guilty. The first was Darryl Armstrong (innocent - rumoured by Emma), the third was Archie Simpson (innocent - accused by Darcy), the fourth Coach Carson (guilty - he made K.C. watch porn and tried to make him have sex with a hooker against his will), the fifth Winnie Oh (guilty - she had a relationship with Sav) and the sixth Grant Yates (guilty - he statutorily raped Tristan and attempted to grope Winston).
- Main article: Paige-Matt Relationship