Dak and Winger share both a sibling relationship, as well as a dragon/rider one.
This section requires expansion.
In "Double Finked", Winger and Dak tested the Rescue Vine Hannahr made for them. Dak kept getting tangled in the vine and putting himself in danger, so Winger suggested returning to the Roost in order to protect his friend.
In "Divewings", Dak and Winger worked together to defend a viking boat from two Divewings and chased them to their nesr. Later, Dak and Winger switched with Leyla and Summer for a day, with Leyla riding on Winger and Dak riding on Summer.
In "Mecha-Menace", Dak and Winger collaborated in putting Haggis out into the light, so that he could see his shadow. The two spent the rest of the day together, watching Magnus' Mechano-Dragon prepare the town for the Spring Festival, as well as the competition between Leyla and Axel Finke.
In "Summer Holiday", Dak attempted to convince Winger to relax, while the Rescue Riders were on a vacation. However, Winger kept practicing with training gear and scanning the island for potential dangers. After fighting eels amd wolves, Winger admitted that he needed a break from adventures, much to Dak's surprise.
In "Puff Enuf", Dak helped Winger train in shooting moving targets. When Winger succeeded, the two headbutted, leaving Dak dizzy. After they found Zeppla, the Puffertail, Dak and Winger took turns in training her to be a Rescue Rider. Later, when the Rescue Riders were stuck in quicksand, Winger grabbed Dak with his claws as Zeppla was pulling them out.
In "Hot, Hot, Hot", Dak and Winger worked as a pair while stalking Aggro around the Roost. Later, after the Fire Fury got stuck in a volcano, Winger tried to reach her but failed due to the intense heat. Dak comforted his friend and even tried to touch him, but quickly retracted his hand, as Winger was burning hot.
In "High Anxiety", Dak and Winger went after Hannahr when Mama Ironclaw was in danger. However, she couldn't help them, as she was afraid of heights. Winger then gave Hannahr a big speech about how she should confront her fears, only to be reminded by Dak that she can't understand him. Winger asked Dak to translate it to Hannahr, but the boy did it less convincing. He apologised to Winger, telling him that he's not as good at giving speeches.
In "King Burple", Dak and Winger came up with an idea of searching for Rocky, after it was lost among a large pile of rocks. Winger held Dak upside down while flying above the rocks, while the boy quickly glanced at the rocks below him. However, their method proved unsuccessful, while they also disturbed Leyla and Summer's method.
In "Charged Up", Dak was very proud of Winger for besting the other dragons at a target shooting competition. He and Winger boasted about the latter's speed and powerful blasts, when Magnus'latest Mechano-Dragon proved to lack those abilities. Dak and Winger then worked together while attempting to destroy machine, by flying fast enough for the Mechano-Dragon to break apart.
In "Belly Flop", Dak and Winger practised diving moves together, enjoying the experience. Later, Winger helped Dak attempt to recreate the recipe for the Seven Spice Seafood Surprise, which had been eaten by Haggis. However, Dak failed to make any of the dishes taste good, so Winger implored him to stop. When Leyla arrived at the Roost and asked what was going on, Winger nudged Dak to tell his sister the truth.
In "Game of Horns", Dak and Winger worked together while helping Duggard in the titular event. When Magnus trapped the Rescue Riders in Slinkwing goo, Dak was able to get out by removing his boots, and freed Winger from the sticky substance.
In this special, Dak and Winger worked together to decipher the clues from the map leading to the Golden Dragon. They watched each other's back when they confronted the pirates seeking the Golden Dragon: Erik the Wretched, Svetlana the Sly, and Waldondo del Mundo.