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Episode 40 The Would be Dragonslayer Aired:
November 7, 1986
The ponies have gathered for a series of events and are enjoying the show thus far as Shady and Gingerbread compete in the Earth Pony Jumping Finals. It's a close series of jumps until Shady edges out Gingerbread at a lake. However, Spike races to them and is in dire need of help. A boy on a camel is after Spike but Whizzer intercepts and knocks the boy off the camel to the ground before shutting out the camel too.
The boy refuses to give up and chases Spike to a flagpole and Spike is forced to climb up.
This time, Masquerade helps and knocks the sword out of the boy's hand, whereby Megan prevents it from being picked up again. Megan wants answers and learns that the boy is named Squire and is trying to slay Spike to do a good deed. Spike isn't amused and notes that he's the exception to the classic fairytale dragons. Squire apologizes as he only wanted to do a good deed and become a knight but his deeds have never gone well and uses a song to explain. The ponies and Megan agree to help him out.
By nightfall, Spike is regretting to help Squire but they arrive at a castle with a female trapped inside and no way to get in thanks to the thorny overgrowth. With a little help from Galaxy, Squire and the others reach the outer wall but Gingerbread finds a door and they head inside. However, there's no indication of anyone needing rescuing and the fairy godmother has arrive to ask what they're doing at the Wedding Feast in progress. Furthermore, they learn that the one normally on quests has retired and they're looking for a replacement.
Megan suggests they leave and the godmother agrees so that's what Megans group does without any further incident. They decide to head back to Paradise Estate to rest but Squire hangs back, figuring he's not cut out to be a knight and throws his sword. To his surprise, a voice calls out in protest. Squire peers behind the bushes to find a tortoise on his back and wants to be righted. The tortoise proves to be too heavy for him to do it alone but the tortoise mistakes the realization as an insult.

Up ahead, Squire's camel suggests meeting Megan more strongly but is first to notice Squire isn't with them anymore. The group return to where they last saw him while Squire gets an idea on how to turn the tortoise over. They peer into the bushes just as Squire rights the tortoise but the tortoise is actually the wizard from before that had decided to give Squire a test.
Squire has passed the test and has been chosen to be the replacement. It's time for Squire and the wizard to go but Squire decides to thank those that helped him first. Everyone says their goodbyes as Squire and the wizard disappear. As the group head back to Paradise Estate, Spike realizes Squire wasn't that bad for a wouldbe dragon slayer and everyone has a good laugh about it.