As Ash heads back to Hearthome City for his long-delayed Gym battle, he's concerned about his own Gligar's battle woes. Even though Ash gives Gligar lots of special training, it just can't get its act together. Gligar finally gives up and flies away, only to run into Gary Oak. Gary offers to help with Gligar's problem, starting by having a friendly battle between Gligar and Gary's Umbreon. Once the battle starts, Gligar panics, and Gary realizes what the problem is: Gligar is overcome by fear whenever it tries to fight.
Gary thinks Gligar should use a Razor Fang to evolve into Gliscor, and Gary just happens to have a Razor Fang he can give to Ash. Once Gligar is a powerful Gliscor, its fear will be a thing of the past! Gligar loves this idea, but Ash says no; he wants Gligar to conquer its fear before it evolves. Poor Gligar gets another shock when Team Rocket springs an ambush with their giant Gliscorbot, snatching Gligar and making a getaway. Ash manages to leap onto the Gliscorbot before it escapes, but that just means Ash and Gligar end up stuck in the same cage!
While Team Rocket celebrates their catch by eating themselves into a stupor, Ash coaches Gligar to break them out of the cage with X-Scissor. With Gligar's help, the two of them then escape across a chasm, and Gligar's confidence begins to build. Just in time, too, because Team Rocket has caught up with their escaped captives! Ash tosses Gligar the Razor Fang and it evolves just in time to save them both from Team Rocket's clutches. In fact, by the time Gary and the others catch up to Ash, Gliscor has Team Rocket pretty well beat! Gary says his farewells and our heroes get back on the road to Hearthome City, now accompanied by a confident new Gliscor!
The episode begins with Dawn placing one of Brock's classic stew pots onto a table, in the center surrounded by smaller plates with salad on them. Beside the table are Ash and Brock, who have just finished preparing the food for the Pokémon. Ash calls over to the group's Pokémon that are playing in a stretch of water nearby to come and get it, which they do in earnest. Brock seems happy at how well the group of Pokémon are getting along and how they seem to be enjoying the food. On ground level, Swinub starts to take too much of a liking to Piplup's food portion but is stopped by the no-nonsense penguin who pushes it back. Turtwig gets between the two bickering Pokémon and stops the fight before it starts, while Ash and Dawn laugh at the squabbling duo. Ash then realizes that Gligar is nowhere to be found and gets up and starts to look around for the missing Pokémon. Ash calls out its name, and is replied instantly by an affectionate Gligar who drops down from the sky and lands straight on top of Ash slamming him to the ground. Ash wonders where Gligar went to, and Gligar starts to use X-Scissor to show Ash that it has been training. Ash is impressed, and Brock wonders if maybe it's trying harder to get stronger after being defeated by Paul's Gliscor. Dawn tells Brock to hush as he's hurting Gligar's feelings and Ash comforts the upset Pokémon by telling it that they'll do some training together soon.
After the group finish their meal, a practice battle between Gligar and Buizel is set up so Gligar can practice some of its moves. Gligar seems confident, before Buizel starts to look at it with an evil smirk. Gligar's confidence starts to waver, but Ash tells it that everything will be fine and that a battle like this is just what it needs. Gligar is satisfied by this, and Ash starts the battle off by telling Gligar to use X-Scissor. Gligar tries hitting Buizel with the attack, but the Sea Weasel proves too fast for it and keeps dodging every attack. Ash then tells Buizel to use Aqua Jet, which it does jumping into the air and speeding towards Gligar with a high powered water attack. Gligar falls to the ground and starts crying, before jumping into Ash's arms and clinging to his head. Buizel continues its attack and smashes straight into Ash, who is far from impressed. Ash asks Gligar what is wrong, but Dawn tells him that he's going about it the wrong way and kneels down to Gligar's level. She then starts comforting it, stroking and gives it a hug which makes Gligar blush and stop crying.
Brock suggests that Ash should maybe use a different Pokémon, and Ash calls out Turtwig to battle against Gligar. Ash tells Turtwig to use Energy Ball, which Gligar manages to dodge but only because it's trying to run away. Ash tells Gligar to use Steel Wing, which it does but falters when Turtwig stares at it ferociously, ready to defend. Gligar then spins around and starts chasing after Ash, who starts to run away. Gligar swoops down, knocking over Ash again with its weight. Ash wonders what is wrong with Gligar and starts to scold the Pokémon who takes it a little too harshly and flies away sobbing. Watching all of this is Team Rocket who are hiding in the bushes. James thinks this is the perfect chance to steal Gligar, who will now be alone and defenseless. Meowth explains that they could capture Gligar and send it to the Boss, who could use it to shield his eyes in the morning when the sun peeks in through the window. Jessie thinks this is a great idea, and the three celebrate at their latest plan.
Back with Ash, Dawn, and Brock we find them calling out for the missing Gligar to no avail. Staravia then flies onto the scene, and Ash asks if the bird Pokémon has seen Gligar. Staravia nods, and the gang follow it to a forest clearing where they find Gligar along with a familiar face: Ash's old rival turned Pokémon Professor, Gary Oak. The two greet each other, and Dawn is instantly awe-struck by seeing 'the poetry guy's grandson' again. Gary asks about Gligar, to which Ash replies that it is his. Ash explains that they were in the middle of a battle when it ran off. Gary smirks playfully at Ash and suggests that maybe Ash isn't able to look after his Pokémon. Ash takes the bait and says that he and Gligar get along just fine. Ash then calls Gligar back to him, but Gligar recoils in fright. Ash grabs a hold of Gligar telling to stop being silly, but Gligar refuses to budge and continues to hide behind Gary. Brock comments that Gligar may not trust Ash anymore and Ash grits his teeth in frustration. Not soon after, the two begin a battle to try to train Gligar up. Ash starts the battle off by telling Gligar to use Steel Wing, which is followed by Gary who tells Umbreon to use Shadow Ball. The attack misses Gligar, but the scared Pokémon recoils in fear and falls back down and lands on Ash. The group then start theorizing on what could be wrong with Gligar, and then the battle starts again. Taking in some of the conversation between the group, Gligar starts warming up to the battle by bouncing on its tail before jumping up to fly. However, once in the air Gligar becomes scared at how high it is and falls back down to the ground and lands on Ash.
At that, Gary says that he has something that may help Gligar, and pulls out a Razor Fang and hands it to Ash, telling him the Razor Fang will make Gligar evolve into Gliscor. Gligar tries to grab the item from Ash but Ash stops it, putting his hand out to stop the over-eager Pokémon telling it that evolution is no substitute for hard work. Suddenly, a large noise is heard from nearby and Team Rocket emerge from the trees in a Gliscor-shaped balloon. The team then recite their usual motto, followed up by Wobbuffet who pops out of its Poké Ball as usual. Gary isn't impressed to see Team Rocket again, who he regards as lame, which annoys the trio to no end. In retaliation to those words, they release the spike of the Gliscor balloon which shoots out and grabs onto Gligar, pulling it in. Ash jumps onto the tail and is pulled towards the balloon along with it much to Team Rocket's annoyance. Ash then calls out Staravia, which is followed by Jessie sending out Seviper to use Haze and Yanmega to use Silver Wind. Seviper appears out of its Poké Ball and releases a deep purple smoke which blinds Staravia, which is followed up by Yanmega which uses Silver Wind to send it plummeting down to the ground.
Soon after, we find Ash and Gligar trapped in a cage with Team Rocket standing nearby their balloon, celebrating their victory. Jessie plans to send for Team Rocket's Delibird to come pick up Gligar and take it straight to the boss. The three then dig into a large pile of tinned fruit. While all this is happening, Gary, Dawn and Brock are busy searching for Ash with Staravia flying above them keeping look out.
Later that night, Team Rocket are sound asleep which Ash tells Gligar is their chance to escape. Gligar nods, and Ash tells it to use X-Scissor to break open the bars on the cage. Gligar does so, but the attack isn't strong enough so Ash tells it to use it again but this time with as much power as possible. Gligar fails again however, and its claw starts to glow red with pain. Ash tells it not to worry, and starts to smash into the cage bars himself. Gligar watches this in amazement. Gligar then resolves to try as hard as possible to get out of the cage and starts to use X-Scissor again. This time Ash notices a change in the strength of the bar, as it appears wobbly at the top. At this, Ash tells Gligar that they need to work together to get out and they both attack the cage bars at the same time which breaks them open. The two then escape from the clearing where Team Rocket had landed and head out on their way back to the gang. On the way they come across an old, rickety bridge, and Gligar jumps on Ash's back as they try to get across it. The wind makes this difficult, as well as the various holes in the bridge which Ash jumps between. The bridge then falls apart sending Ash and Gligar falling, but Ash manages to grab a hold of the rope holding the bridge together and merely swings and hits the rock facing.
Back at Team Rocket's camp, James wakes up from a peaceful sleep and is horrified to find Ash and Gligar gone. He then tries to wake up Jessie and Meowth. Back with Ash, we find that he and Gligar have managed to climb their way back up to the top of the cliff. Ash looks around, and notices a tree near the edge of the cliff not far from where the bridge used to stand. He tells Gligar to try to knock it over, which it tries to but fails. Ash asks Gligar if it's okay, but Gligar simply gets back up and tries again, jumping into the air and smashing into the tree again. This time, Gligar finally succeeds and the tree falls, forming as a bridge between the two cliff edges. Ash is proud of Gligar, and tells it that it's earned the Razor Fang that Gary gave him before. Gligar is overwhelmed with happiness and hugs Ash, but the happy moment is interrupted by Team Rocket who appear in their Gliscor balloon. Ash tells them to leave them alone, but is ignored as Team Rocket is set on stealing Gligar for Giovanni. The Gliscor tail shoots out again, but Ash jumps in the way of it and is captured instead. Holding Gligar in his arms, he tells it that he's going to let it go so it can escape. He then does so, and Gligar falls down below. Ash then falls himself, and falls past Gligar due to being less air-resistant. Gligar notices Ash falling below and tries to grab him but isn't fast enough. Ash throws Gligar the Razor Fang, which Gligar catches, causing it to instantly evolve into Gliscor. Ash smiles at seeing his Pokémon evolve, but then remembers he's falling and starts to scream uncontrollably. However Gliscor is now a lot faster than before and grabs Ash and uses its tail to cushion the blow to the ground. Ash thanks his new Gliscor for saving him. Team Rocket then float down from above, and the team seem confident that they can still capture Gligar in its evolved state.
Ash tells Team Rocket that Gliscor belongs to him and isn't going anywhere with them, and then has Gliscor to use X-Scissor, which smashes into the Gliscor balloon tail and knocks it back. At this, Gary, Dawn and Brock run onto the scene and call out to Ash. Dawn is amazed to see that Gligar has evolved, and Brock congratulates it for doing so. Team Rocket then shout out to the group below angry at being ignored, and Meowth sends out the claws of the Gliscor balloon mecha. This is deflected once again by the real Gliscor's X-Scissor attack. Ash then tells it to grab a hold of a tree branch and charge up its power, which it does, before flinging itself of the tree and using Steel Wing aimed at Team Rocket. James smirks, saying that Gliscor can't beat their mecha balloon's power. Meowth then activates the balloon's Steel Wing mode, which emulates the real Pokémon's attack. The two 'Gliscor' face off, both hitting each other at the same time. Ash's Gliscor wins out, and Team Rocket's splits into two halves and falls down to the ground. Meowth gloomily remarks that they won't have a Pokémon to give to Giovanni after all, but Jessie screams at it to help them get the mecha back together again. Ash then tells Pikachu to use Thunderbolt, which causes the Gliscor balloon to explode and sending Team Rocket blasting off again. The group are relieved to have sent Team Rocket packing, and the sun then rises as if to agree with them. Ash and Gliscor watch the sunrise and give each other a smile, the rift between them healed and with a stronger bond than before.
Soon after, we find Ash, Dawn and Brock saying their goodbyes to Gary. The young researcher seems impressed with Ash, and Ash thanks Gary for the help he has given them, including giving him a Razor Fang. Suddenly, Dawn starts to recite a Pokémon poem thinking that, like his grandfather, Gary is a big fan and expert on them. Dawn seems proud but the rest of the group smile and sweatdrops. An instant later this is forgotten about, and Gary bids the group farewell, wishing everyone good luck in their goals. They then wave goodbye to him, before heading out on the road to their next adventure.