But this time, they decided to tape up Fish while he was standing up.
"When I think about it, it seems like I was hit by a car," Fish explained.
Fish doesn't remember much from that day.
He and two buddies had gone to Renton Academy on a Saturday, where they had duct taped his arms and legs.
"When he fell, he hit the corner of the window frame," Skylar's mom, Sarah Fish, said. "It crushed his whole eye socket and pinched off nerves in his eye."
Skyler Fish doesn't know if he'll ever get his vision back in that eye.
His head also slammed into the concrete, causing a brain aneurysm.
He had to get 48 staples on his head.
"It was really scary, just seeing my son like this." Sarah Fish added.
Skylar's mother wants to warn others about the duct tape challenge.
"I want people to stop and think that there are so many risks to any of these challenges," she said. "They're dangerous."
Skylar Fish left for Seattle Children's Hospital on Monday for the rest of his recovery.
He said he wants something good to come out of this.
"Teach other kids not to do it," Skylar Fish explained. "When I think about it, I become sad and then really happy, because I'm happy, because I survived it. I almost died."
Renton police looked into what happened. Sarah Fish said they're closing the case, because it appears what happened was simply an accident.
Skylar Fish's family has created a crowdfunding campaign to help with his recovery costs.