The episode begins with Peter and Hannah out on their daily morning jog turned friendly race. While stopping for a break, they happen upon Bob Archer and his Lawrence Hastings Prep students (the rival school) on a bike ride thought the woods in training for the X-Challenge Race. Bob stops to say hello to them and he and Peter get to talking. Peter mentions that he's putting together a team of his own for the competition and Bob laughs at the idea, adding that Peter's faith in those "delinquents" is sweet, but this is a real competition. Peter then challenges Bob to a bet that the Cliffhangers will finish before Bob's team, loser buys dinner. Bob accepts. Hannah is reluctant, stating that Scott hasn't adjusted yet and implied that the rest of the Cliffhangers don't exactly know how to work as a team. Peter thinks this is precisely why they should enter..

Scott and Juliet spend their morning making out in the empty dining hall and almost get caught upon Peter and Hannah's return. This is also where we learn that Scott and Juliet have become a couple.

Peter calls a group meeting and explains the competition to the Cliffhangers including all the rules and regulations. There are three parts to the race - kayaking, mountain biking, and ending with a run through the woods with a map and compass. Everyone must finish each part together as a team before continuing on to the next part of the race. Peter appoints Kat as captain of their team. She is enthusiastic about the competition but everyone else wants no part in it. She quickly changes their minds pointing out all of the positive aspects of the race, during which Scott decides he's had enough and leaves. Juliet goes after him. Kat tells Peter that Scott's attitude stinks and she doesn't want him on the team. Peter explains that he needs to learn how to trust the rest of them and this opportunity may help him do that. Meanwhile, Juliet talks to Scott asking him to participate in the race, stressing how much of a great football player he was and how his athleticism would be an asset to the team. He yells at her to stop telling him how great he was, adding he's nothing now.

The training begins with a strenuous run through the woods. Next Kat is taught how to read and use a map and compass. Later, while learning rock climbing, the Lawrence Hastings team shows up during their bike riding training. Bob and Peter decide to raise the stakes of the bet, making the loser have to sing in front of everyone at the post-race barbeque.

The next morning, training includes mountain biking and kayaking. Scott participates working hard, but still not working with the group. After training, Kat and Scott get into an argument about the group in which Scott tells them all how horrible they are. Peter talks to Scott about the situation. Scott tells Peter that "they don't know how to win." And Peters explains that's basically because they don't do a lot of winning around there, the do a lot of "just getting by." Peter tells Scott to stick with it and he might learn something from it, to which Scott asks, "What am I supposed to learn from losing?" Peter replies, "What have you ever learned from winning?" Walking away from the conversation, Scott runs into Shelby who starts flirting with him, saying how he loves the fact that he has "two girls crushing on him" and that she could help him decide between the two. He matter-of-factly tells her that he doesn't "go for used cars."

At the nursing home Kat works at, she runs into Michelle, one of the Lawrence Hastings team members. She invites Kat to go meet some of her friends at a restaurant, but Kat declines telling her she can't miss the bus back to Horizon. Michelle reassures Kat that she'll be back in time, which of course she isn't. As punishment, Peter takes her out of the race, replacing her with Scott as the captain. Scott argues with Peter about his decision, saying that the race is really about Peter and his ego - about Peter wanting to prove Horizon is better that Lawrence Hastings. Peter admits that he is too competitive and he does want to win.

The race begins with kayaking and Scott pulls out in the lead but stops to help the group as they get tangled up in each other. They all reach the first checkpoint together and begin the second part of the race – mountain biking. Again, Scott leads as the rest of the Cliffhangers struggle to keep up. Scott pulls way ahead, passing the Lawrence Hastings kids, leaving his group behind. He reaches the checkpoint first but is unable to continue on without the others, and once again Lawrence Hastings takes the lead. Scott sits and waits. The rest of the team finally shows up but need to stop and rest before continuing on. Thoroughly irritated, Scott throws down the extra map and compass and takes off, telling anyone who wants to win to go with him now. He continues alone, leaving the rest of the team to get lost trying to keep up with him.

While deciding in which direction to go, Auggie falls down a small cliff and injures his ankle, twisting it. Juliet radios for help on the emergency hand radio she was provided for the race. Upon reaching the next checkpoint, Scott learns that one of his teammates is injured. Instead of going back to help them, he continues with the race alone. Peter and Hannah also learn of the injury and Hannah goes to help. Soon after, both the Lawrence Hastings team and Scott cross the finish line, but without the rest of his group, the other team wins.

Peter yells at Scott about having left the others behind. Scott tells him it's not his fault the others didn't make it, telling Peter if he's going to blame someone, blame himself - it's his school. Peter asks Scott if he had ever lost a game or missed a pass. Peter tells him that most of those kids have never won anything in their whole lives and now thanks to Scott this is just one more thing they've failed at. Peter tells him that he was on a lot of teams once too and he knows how good it feels to be a part of something, even when you lose. Peter tells Scott how he could have helped them feel that way, but instead didn't believe in them and left them behind. Peter leaves and Scott begins to have flashbacks of a game he played where he missed a pass and ended up losing the game. After the game in the locker room, even though they lost, his team was there for him and supportive of him. He then decides to go after the group and bring them all back to cross the finish line together.

Scott finds them and apologizes and tells them that he can help them make it to the finish line. Hannah shows up to help Auggie, but he decides they should all finish the race together, even if they already lost. They all make it to the finish line where Kat and Peter are waiting for them, cheering. Kat congratulates Scott on getting them through the race, be he tells her that they were really her team.

That night at the barbeque the Cliffhangers have to cook dinner for the winners. In the lodge Scott and Shelby talk and he apologizes to her for insulting her. She asks him if maybe they could hang out together and maybe her could find something he likes about her. He says sure. Juliet finds Scott in the kitchen preparing food and they start kissing. Shelby ends up witnessing it and is apparently very hurt by it.

Outside, Peter is now called upon to sing an unknown song picked by Bob, his result of losing the bet. The music starts and embarrassed, Peter starts singing YMCA by The Village People. Scott pulls Juliet up on stage with Peter and the rest of the groups follows. They all sing the chorus together, laughing and making fun of themselves.