A motivational sports series such as Run with the Wind is unfortunately not without heartbreak of sorts.
All spoilers are unmarked.
- Haiji's collapse in Episodes 9-10 causes everyone on the team to feel guilty in some way, as they realize Haiji's been doing a lot more work than they thought. Kakeru in particular is guilt-ridden, thinking his cynicism and constant nagging is what lead to it.
- Episode 11 shows that the ever-so organised Shindo struggles more than he lets on, including being dumped by his girlfriend who understandably is unhappy that they never see each other. He feels down that he still can't get an official record and he frequently laments that he isn't all that strong, although everyone else is quick to say otherwise.
- Episode 16:
- Haiji's grimace when his injured leg acts up towards the end of the race. He manages to finish without any trouble but is seen with an ice pack on it afterward. In an unadapted moment of the novel, a frightened Kakeru notices Haiji is in pain and rushes to his side as soon as he finishes racing, and he feels guilty when Haiji tries to brush it off and compliment him on his results.
- The sad reality for many of the racers is shown, with quite a few having to dropped out due to injury or simply being no longer able to run. Prince is just barely luckier than those racers, running to the point of throwing up and having to be carried away after he finishes to get treated for exhaustion.
- Episode 17 shows one of the few moments of in-series racism, as two passerbys spot Musa together with Kakeru and express their disgust that the Kansei team isn't fully Japanese. Kakeru is incredibly angry, despite Musa insisting it doesn't bother him.
- There's a brief flashback of Haiji and Fujioka during high school in Episode 18, at some point after Haiji's injury. Fujioka looks on in concern as a glum Haiji speaks to the coach while wearing a knee brace, presumably about his future as a runner, and afterward Haiji laments that he just isn't strong.
- Episode 20: The entirety of Shindo's turn at Hakone. Despite being very sick and in no condition to be running (not helped that he's running uphill, something he would easily do at the top of his game), he refuses to resign from the race and pushes himself to the point of collapsing at the finish line of Day 1. The other members can barely watch, the coach continuously tries to persuade him to forfeit, and Joji (who ran before him) blames himself for not running faster so he could put less pressure on Shindo. The most heartbreaking part about this is perhaps his family back at home—they've gathered together to watch him on TV and celebrate his participation in this special event, only to instead watch on in horror as their boy breaks himself.
- Episode 22 hits close to home for many viewers with King's monologue, where he regrets not having an eventful college life and feels like he has to act like something he's not to protect his insecure self.
- In Episode 23, Haiji is running the last leg of his section and sees Kakeru waving him down, in a beautifully heartwarming moment, and then his knee acts up. Internally, Haiji is screaming in agony, but on the surface he appears fine, but Kakeru notices and begins to tear up, left being only able to watch what is Haiji's last moments as a competitive runner before he collapses into his arms. In the Distant Finale, Haiji can be seen with a slight limp, showing that the Ekiden has left permanent damage to his knee.
