The Underdogs Books in Order

The Underdogs series is Kate Stewart’s love letter to late‑night college apartments, underfunded marching bands, and the athletes who are supposed to have it all together but really, truly do not. Each book stands on its own, but the three stories are tightly knitted through a shared friend group and a lot of overlapping chaos.

In The Guy on the Right, Theodore “Teddy” Houseman has finally shed his high‑school image as a band geek no one notices. At the University of Texas at Galveston, he is thriving in the marching band and, for once, feels like he might be the hero of his own story. The problem is his roommate, Troy, is a campus football god, and everyone assumes Teddy is the comic relief. When Teddy quietly falls for their new neighbor, Laney, he is determined not to be sidelined. The book is equal parts hilarious and heartfelt as he tries to prove that the so‑called nice guy can, in fact, get the girl.

The Guy on the Left gives Troy his turn. On the surface, he looks like the archetypal quarterback womanizer, the guy people blame when things go wrong. In reality, he is a young father doing his best and living with the consequences of one very complicated night. The story unravels the lie that has defined his reputation, showing how he fell for his son’s mother and how badly he handled the fallout. Told as a kind of confession, it is about owning your mistakes and fighting to become the man your child believes you are.

The Guy in the Middle rounds out the trio with the friend caught between those two extremes. A driven athlete who was born to play and bred to win finds his carefully mapped future threatened when he falls for a woman whose dreams do not line up neatly with his. Their relationship forces him to question whether success is measured in trophies, in contracts, or in the life you build after the stadium lights go out.

Across all three books, expect sharp banter, messy group dynamics, and a lot of found‑family warmth. Side characters drift in and out of each other’s stories, so you will see relationships evolve from several angles. The series also plays with the idea of perspective: how campus gossip, first impressions, and old grudges can hide the truth about who people really are.

You can start with whichever hero intrigues you most, but reading in order lets the extended epilogue in the final book land with maximum payoff, tying up loose ends for the whole crew.