Scenario:
The episode starts with the gang travelling on a boat so they can easily cross the sea that is between them and their next destination. Having just won the Symbol at the Battle Pike, Ash is admiring his Symbol case which now contains 4 symbols. Brock says the next battle facility, the Battle Palace, is on Metalica Island not too far from here.
However, there are few more island stops on the way, the first being Potpourri Island which lies dead ahead, and is where the boat is heading. Meanwhile Team Rocket are following the boat in their Magikarp submarine, determined to keep up with Ash and co. However, they are having their usual argument because Jessie is refusing to pedal because she says she is tired, despite James and Meowth being far more exhausted than she is.
The gang reach the island and head towards the nearest Pokemon Centre. They notice some young Pokemon in a paddock next to the Pokemon Centre and comment on how cute they are. Nurse Joy comes out to meet them and just as some other trainers pass them, talking about a competition that they are entering. They ask Nurse Joy about it and she says that the island holds a Pokemon Orienteering Contest for trainers and their Pokemon to encourage teamwork. She says the prize is a teamwork medal and some of Potpourri Island's famous fruit. The gang ask Nurse Joy if they can enter and she says they can. Team Rocket have been listening in on the conversation from nearby and like the sound of the competition's prizes. James wants to win the medal whilst Jessie is more concerned about the fruit and the idea of a good meal.
That evening, sitting on the balcony of their room in the Pokemon Centre, the gang talk about which Pokemon they should enter the Contest with. Ash says he will stay in battle mode and enter with Pikachu. May and Brock decide to enter with their newest Pokemon, Eevee and Bonsly, in order to bond with them better. Max who has no Pokemon of his own asks May if he can borrow her Munchlax in order to compete, to which May agrees. The group then jokingly tease each other about how they are going to win.
The next morning, Ash, Brock and May leave the rest of their Pokemon in the paddock next to the Pokemon centre while they compete in the Contest. Nurse Joy displays the prizes, a shining gold medal and a large variety of fruit and explains the rules to the competitors. They may only use their map and their compass and the first person to reach all 5 locations, stamp their map and return to the Pokemon Centre will be the winner. Munchlax is psyched up after seeing all the fruit and looks eager to start. After viewing the prizes James, partnered with Mime Jr, is determined to win the medal whilst Jessie, partnered with Meowth disguised as a Sneasel, has a burning desire to get the fruit. Nurse Joy starts the Contest and the competitors race into the woods.
Ash decides to go to the location that is furthest away from the finishing point, which is Rainbow Falls whilst his friends have different ideas. May and Eevee head to the cliff that is overlooking the ocean. Bonsly is proudly charging ahead as Brock tells to save its energy, he decides the two of them should head towards the 300 year old giant tree. Max is having little luck in his attempt to win the competition as Munchlax dashes off aimlessly as he desperately tries to keep up. Meanwhile, James examines his map a he and Mime Jr decide to head to the Moon Rock, whilst Jessie and Meowth come up with their own strategy to walk in a straight line and hope luck takes them to each location.
To reach the separate locations the teams have to cross a variety of obstacles. Ash and Pikachu cross rift on a log perched high above a fast moving river, a strong gust of wing nearly blows them off but the manage to cling on a crawl the rest of the way. May and Eevee are crossing another river on some steeping stones. Despite being careful, May slips and falls into the river and is dragged downstream by the powerful current. Eevee jumps in as well to stay close to its trainer. Brock is following his compass towards his first location when he sees Nurse Joy who is also competing. Love struck, he attempts to get to Nurse Joy but Bonsly, annoyed by his actions, attacks Brock and sends both of them flying. James is climbing a small cliff with Mime Jr in order to reach the Moon Rock. They reach the top and find themselves at their first location. He stamps his map as proof, noting that a Lunatone is quite a good choice as a symbol. Max is still having the least luck of all the teams as Munchlax is still shooting around the island without paying any attention to the map. Jessie and Meowth's strategy has hit a rock as they have reach a cliff edge and have nowhere left to walk, deciding to ditch the straight line strategy.
Ash and Pikachu reach their first location , Rainbow Falls which consist of a waterfall and Remoraids shooting water in arches over a walkway. Ash runs to the end of the walkway and stamps his map, noticing it is shaped as a Remoraid. Brock and Bonsly have also reached the 300 year old giant tree, which towers metres above them. They climb over its roots and reach the stand to stamp their map, with Brock exclaiming it is shaped like a Pineco. Max is starting to fall behind as Munchlax is still running rampant, as he tries to keep up. Meanwhile May and Eevee have finally pulled themselves to the river bank as they reached as part of the river where the current wasn't as strong. May apologises to Eevee, but turns her head to see the cliff overlooking the ocean, the location they had been heading for. They run the last towards it ands May admires the view before stamping the map.
Jessie and Meowth are now getting annoyed as their change in strategy has somehow got them to the top of a tall rocky outcrop. Jessie is starting to get frustrated at their lack of success with Meowth trying to calm her down. She decides to give up the competition and let James do all the work as if he wins they will still get all the fruit. Elsewhere, Munchlax has finally stopped running and Max is examining in the map to try and get them back on track. However Munchlax has now fallen asleep which severely dampens Max's spirits.
Ash and Pikachu are heading to their next location when they unexpectedly fall down a pitfall trap. Jessie and Meowth are watching from nearby and snigger at their success, having decided to knock down the competition to give James a better shot of winning. Munchlax has managed to get away from Max who is now searching the woods for it. He has no luck but comes across Eevee which leaves him wondering where May is. May is nearby looking for it omes across Munchlax before she sees Max and Eevee in the path ahead. May tells Max to take better care of her Munchlax but annoyed, Max tells her she should have been taking better care of Eevee. Max asks May how many stamps she has and she says she has 1. Max is worried by this and grabs Munchlax and runs off. May calls after asking how many he has but he doesn't tell her. Ash has now reached the cliff overlooking the ocean and stamps his map, noting how cool the Kingler stamp is.
Back at the Pokemon Centre, the rest of the gang's Pokemon are playing in the paddock with the other baby Pokemon. Donphan is allowing Aron, Smoochum and Igglybuff to use its trunk as a slide whilst Marshtomp and Wooper roll around on the floor. Combusken, Chikorita, Corphish and Azurill are also playing as Grovyle stands guard next to the collection of fruit that will be awarded to the winner of the orienteering competition.
Meanwhile James is heading towards the Suspension Bridge when Jessie and Meowth approach him saying that they know a short cut. They take him to the bottom of a huge cliff saying that the bridge is close to the top of it, and that the exercise will do him good. James, however, is furious that they even suggested it saying that he might consider it if it was just him but not when he has Mime Jr to look after. May has now reached her second destination, the Moon Rock, and stamping her map as proof.
The separate teams now take a lunch break, with Ash eating a sandwich and Pikachu eating some Pokemon food, while Munchlax devours his large helping of Pokemon food before taking Max's sandwich. May gives Eevee some food and Brock bottle feeds Bonsly. The Team Rocket teams, who are always in short supply when it comes to food, share a biscuit between them and their Pokemon. Both Jessie and James unevenly split their biscuits but whilst James and Mime Jr insist the other takes the larger piece, Jessie and Meowth fight over it.
Now rested, the teams continue the search for the remaining locations. May and Eevee take a zip-line down a hill to save time but fall afoul of another of Jessie and Meowth's pitfall traps, who are watching from behind a bush a snigger at their success. Max and Munchlax are starting to catch the other competitors up but now have reached a river that they need to cross. With no obvious way visible Max uses a long stick to vault the two of them on to the other side. The make it to the other side but fall into another hole as they land. May has now reached the Suspension Bridge and stamped her map, as she is leaving Max arrives on the two of them stop and ask each other how many stamps they have got. May says she only needs one more which depresses Max and he needs another two.
While they are distracted Jessie and Meowth cut both ropes that tie the bridge to the outcrop causing it to fall. As it collapses, Ash and Brock hear their shouts and rush to help. With two less competitors for James to worry about, Jessie remarks that he a guaranteed to win the fruit now. Meowth suggests instead of waiting they steal the fruit now, to which Jessie thinks is a good idea. They head towards the Pokemon Centre and fire a net at Ash and Co's Pokemon so that they cannot interfere in their plans. Meowth also coners the baby Pokemon so Jesise can capture them. However Swellow, who was not caught in the net goes to try and find Ash and co to alert them to what is happening.
Ash and Brock get to the suspension bridge just as the rope holding it the to the other side snaps, but the grab it in time and pull them to safety. They discuss how they all seem to be being targeted and wonder if someone is trying to sabotage them. Just then Swellow finds them. Ash realises something is wrong and Swellow leads the gang to the Pokemon Centre to stop Jessie and Meowth. When they get there Ash confronts Jessie and Meowth who are carting away the fruit and about to make their getaway. The two of them recite their motto but the rest of the gang use this distraction to free the Pokemon and reclaim the fruit. When the motto is finished Jessie and Meowth find themselves facing the entire gang without any of their acquisitions. In an attempt to get them back, Jessie sends out Dustox to fight Ash and co, and Ash calls on Donphan to stop them. Jessie orders it to use Tackle but Ash has Donphan fight back with Take Down. Dustox is knocked down and Ash has Donphan use Hyper Beam to send them blasting off.
Later that day the competition has ended and James has emerged victorious. He Is presented with the teamwork medal, now containing a picture of him and Mime Jr, and the fruit. Jessie smirks that even alfter their plot was thwarted they will still get there hands on the fruit. However, Nurse Joy asks James if he would consider donating the fruit to Ash and co after they saved all the Pokemon at the Pokemon Centre. James agrees, shocking Jessie and Meowth, saying that he doesn't care about the fruit, he just wanted the medal.
That evening, the gang are eating are eating some off the fruit as Max says it it was disappointing how none of them managed to win. They however agree it was good fun and gave them the chance to spend more time with their Pokemon. As May starts talking about how she wants to start introducing Eevee into contests, Nurse Joy comes over having overheard what she said. She tells May that there is a contest held on the island nearby in Wisteria Town. Delighted at this May is instantly psyched up and determined to compete in the contest.
The episode ends with May how aiming to win her third Kanto Ribbon.
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