In 99 Problems (1), Riley is in the hallway signing up for the football team, when he meets Drew, who asks if he can borrow his pen. Zane comes over to sign up. Riley asks if he's serious about joining the team, Zane confims that he is, saying "The team needs a kicker, and I gotta show that gay guys can play sports." Drew is surprised about how open Zane is about his sexuality. In the next scene, Drew and Riley are in Algebra. Riley learns Drew is trying-out for QB1, and Riley doesn't like the idea as he was trying out for the position himself. Riley and Drew are then seen trying to out do each other on exercise equipment in the gym, as their coach watches. Coach Armstrong tells Riley that he has a good shot at making QB1 this year. Riley, confident about getting the position, teases Drew by telling him that there is always next year. One of the football players starts to make fun of Zane as he walks in, but he stands up for himself. Drew says to Riley, "It won't be good when we play against other teams and they find out our kicker kisses dudes." Riley and Zane start talking about their love life privately in the gym after the others have left, and Drew overhears their conversation about the "Two Riley's Theory". With all the information he needed to blackmail Riley, Drew walks away with a grin on his face.All of the football players are in the gym while the Coach Armstrong is talking about the next day's tryouts. Drew suggests they have a BBQ in the parking lot to raise school spirit, and everyone's likes the idea. When they are all ready to leave, Drew looks at Riley and says, "Oh, and guys don't forget to bring a date". At the BBQ, Riley walks up to Drew and introduces him to his "date" Marisol. When he mistakes her name as Marilyn, she walks away. Riley asks him why he doesn't have a date, and Drew tells him he doesn't know any of the girls at Degrassi just yet. Drew makes a gay joke to Riley, which angers him. Riley and Zane start talking, and they get into a fight. Zane breaks up with Riley, not even wanting to be friends. Drew comes over to speak to Zane, and when Riley answers for him, Zane becomes angry and walks away. Drew tells him to stop denying that he is gay, and Riley gets even angrier with him about his "jokes". Drew admits he wasn't joking and threatens Riley, telling him to step aside for QB 1, or else he'd tell the entire team Riley was gay. Wanting revenge, Riley starts up a conversation with Owen, another football player, and ask him what he thinks about the new guy (Drew). Owen thinks he's a cocky bastard, and Riley suggests they teach the new kid "a few lessons".
In 99 Problems (2), Drew arrives at Degrassi for a morning football practice, and Riley and Owen sneak up behind him pin him to a flagpole, strip him of his clothes, wrap him to the pole with tinfoil, and duct tape his mouth shut for everyone to see. Mr. Armstrong later gets him down. There is a football team meeting called in the gym and Drew's mother Audra is there. She threatens that if no one owns up to the hazing, that she'll go to the school board. Drew says that the criminals had masks on and that he couldn't see him. Later, Riley confronts Drew asking why he covered for them. Drew tells him that he'll continue to keep it a secret as long as Riley steps down for QB 1. Riley considers it, but decides not to and he earns the spot. Audra keeps her promise, and calls the school board. They suspend the team from playing until someone is punished for hazing Drew. Riley admits to his mistake, and the team gets to play. Drew takes his position, and Riley has a five game suspension. Drew agrees to keep Riley's sexuality a secret.
In Still Fighting It (2), Drew confronts Riley, telling him that the whole school is wondering if he's gay, then notes it's none of his business and walks away.
In Purple Pills (1), Drew sticks up for Riley when the team is betting on him being gay. Drew tells them to all knock it off when they start fighting because they won the bet. Later he is also celebrating the team's victory of winning their last game of the season.
- They both got involved with drugs while on a sports team.
- They have both been on a date with Marisol Lewis, but haven't been in a relationship with her.
- They both fought to be QB1 while on the football team.
- They both had a conflict with Owen Milligan though Drew ended up becoming friends with him.
- Originally, Drew was supposed to be a bisexual character and was going to have feelings for either Riley or Zane but the idea was scrapped and Drew was instead straight and rivals with Riley.
- They both had an interest in Fiona Coyne, but only Riley dated her.
- Both have kissed a "good girl": Riley kissed Anya MacPherson while Drew kissed Clare Edwards.