Holly J. and Derek formed a dislike of each other early on in Season 7. Due to both of them at the time being disliked by the most of the student body, they never missed a chance to mess with each other.
In Jessie's Girl, Holly J. insults Derek by calling him ugly.
In Uptown Girl, When Holly J. confronts Danny, Derek go behind Holly J. and mocks her.
In Fight the Power, when Jane became a part of the Degrassi Football Team, Holly J. defended her when the guys were making fun of her. When Danny, Derek, Bruce and Riley Stavros were wearing offensive shirts with the phrase 'Sorry I dropped the ball, it's my time of the month' and Derek showed them to Jane. Holly J., Mia and other Power Squad members come in and stick up for her by telling them to take the shirts off. Derek replies that she likes it when he takes his shirt off, and Holly J. responds that she doesn't know what's worse, the shirts or Derek shirtless.
In Heat of the Moment, when Bruce the Moose led the cafeteria in chanting "I Hate Holly J.", Derek joined in. He later walks up to Alli Bhandari, Holly J., and Anya, he than shows the rope (in reference to the comment "Want to strangle her? I'll bring the rope" about Holly J. and says "I'll bring the rope" and laughs.
In The Curse of Degrassi, Mia Jones is angry that Holly J. is taking so long to get the raffle tickets, and she says Holly J. is just going to take credit for all their work. Jane Vaughn and Danny Van Zandt tell her to calm down, and Derek decides to go looking for her. Derek and Sav Bhandari manage to make fun of Holly J.'s ponytail, but Sav becomes whipped when he realizes that he made fun of Anya MacPherson as well. Holly J. has apparently already been raffled. She is standing in the middle of the hallway, a complete mess, and the lights are going crazy. They become normal again when Derek walks in, however. Derek tells Holly J. everyone is mad at her for being a lazy princess, to which Holly J. replies, "You're the princess." Derek laughs at her comeback, and Holly J. asks him if he enjoys picking on the weak. Derek fakes a compliment, but is scared when Holly J.'s eyes turn pitch black. Derek cries out in pain when Holly J. lifts him up by his neck and begins to strangle him. He begs to be let go, but Holly J., snaps, in Rick Murray's voice, "I told you not to call me that. My name is Rick."
- Both are adopted.
- Derek also had a conflict with Holly J.'s best friend Jane Vaughn.
- Both at some point were disliked by majority of the students.
- Both did something to Leia Chang in the opening credits:
- In Heat of the Moment, Derek joined Alli Bhandari's anti-Holly J. Facerange group "I Hate Holly J."