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At the fifth hole, Sopcholes has to putt his ball through an uneven green with a {{p|Spinarak}} and several Alolan {{p|Diglett}} acting as obstacles. He starts running some calculations, but {{TP|Sophocles|Togedemaru}} promptly puts the ball on the move without waiting, successfully avoiding the obstacles and putting the ball into the cup. The Caddie Expert says his 90 years of experience could've offered a better way, doing his best to ignore Katsuo chomping down on him. At the sixth hole, {{an|Lana}} has her {{TP|Lana|Brionne}} create a bunch of balloons. The [[Pokémon category|Pop Star Pokémon]] does as told and also starts singing, with the class's Pokémon and the nearby [[wild Pokémon]] all joining in on the singing and dancing. To Kahili's surprise, even Katsuo joins in after being asked by Pikachu, saying that she hasn't seen it acting like this in a long time. When Kukui points out that Katsuo must be happy to see her having so much fun, Kahili realizes that Katsuo must've wanted her to come play PokéGolf with these children to cheer her up. One of Brionne's balloons lifts up Lana's golf ball, and she hits it right next to the cup in the putting green.
Through the following holes, the class continues to make progress, with Kiawe swinging his ball over a group of Exeggutor, Lana using a combination of Brionne's {{m|Surf}} and [[Nagisa]]'s {{m|Tackle}} to move the ball, and LanaLillie using [[Snowy]]'s {{m|Powder Snow}} to create herself an icy slope to move her ball close to the cup without needing to try too hard. Impressed by everyone's performance, the Caddie Expert offers to take them to the "Demonic Hole 10", which turns out to be located in a windy canyon, with the putting green standing high above them on a small platform. Any ball that fails to go into the cup here will fall into the valley below, making this course very hard. The Caddie Expert offers to make a demonstration, pulling out a [[Poké Ball]] from his golf club bag and sending out a {{p|Krabby}} to be used as his club, much to everyone's bafflement. He takes a hold of Krabby and swings it like a golf club, sending his golf ball towards the green, but just then, the wind picks up, pushing the ball down into the valley. Rotom realizes that the Caddie Expert just showed them an example of how to fail, which he confirms to be true, saying that even the best of players can end up like this after just one misstep. He then challenges Kahili to do this challenge, as she's a pro golfer. Despite Rotom saying that the odds of getting the ball into the hole here are almost nonexistent, Kahili accepts the challenge.
As Kahili and Katsuo prepare for their swing, Ash and his classmates give encouragements to her from the background, and she thanks all of them for their moral support. Filled with confidence, she strikes the ball as hard as she can, and Katsuo uses Tailwind to speed the ball toward the green. However, the wind in the canyon picks up again, and the ball starts falling back. Not hesitating for a second, Kahili picks up Katsuo by its legs and aims it at the falling ball. Katsuo's beak starts heating up, and Kahili commands it to use {{m|Beak Blast}}, firing a massive beam that sends the ball hurtling back towards the green, successfully landing it in the cup. As everyone else celebrates Kahili's success, the Caddie Expert walks away, saying to himself that there is nothing left for him to teach her at this hole, and that he'll be waiting for her at the "Demonic Hole 11".