Four Roads Diverged in a Pokémon Port! (Japanese: サトシＶＳケンゴ！それぞれの船出！！ Ash VS Kenny! Respective Departure!!) is the 23rd episode of Pokémon: DP Sinnoh League Victors.
Ash looks to his final badge he won recently. He, Brock and Dawn are going to ferry, which will take them to Lily of the Valley, where Ash needs to enter the Sinnoh League. To their disappointment, the boat left just a while ago, as the next one comes tomorrow. Suddenly, they hear Kenny, who trains his Floatzel. Floatzel uses Whirlpool and follows with Aqua Jet, which binds it. A woman near him comments that was pretty good. Ash and Brock recognize the lady, as she is Jasmine, the Gym leader of Olivine City. Brock flirts with her and Croagunk comes out and stabs him, even if he met her before. Jasmine recognizes Ash and gets introduced with Dawn. Kenny heard what happened and feels a bit sorry for Dawn for not becoming a Top Coordinator. Team Rocket watch and Meowth believe Floatzel would cool the boss down at hot nights. Ash and Brock are surprised to hear Jasmine gives opinion on Kenny's Contest moves, as she is a Gym Leader. Jasmine believes one needs to gather experiences from all kinds of things; one of these things are the Contests. She left the gym to an old friend of hers to watch while she is absent.
Brock admires her, as she wants to get stronger, which Jasmine knows it is the job of every Gym Leader. Kenny asks what is Dawn going to do next. When told she is going to support Ash at the League, he asks her what next. Dawn admits she has not thought about it yet, but suddenly, Floatzel gets captured by Team Rocket. Suddenly, an Infernape uses Overheat, which makes them blast off. Flint comes and lets Ash know that Volkner said hello to them all, as Ash brought his old self back. Jasmine comes and introduces herself to Flint, wanting a battle to improve her skills. Flint accepts, while Ash knows this is going to get awesome. Flint uses Infernape, while Jasmine sends Steelix. Ash knows he had a rough time with its Iron Tail, but overcame that. He sends Infernape to watch how Flint's Infernape battles. Kenny seems worried, but supports Jasmine. Steelix uses Iron Tail, but Infernape dodges. Steelix attempts once more, though Infernape deflects it. Steelix uses Sandstorm, but Infernape repels the attack. Steelix goes to bite and gets taken back (and defeated) from Flare Blitz.
Flint lets Jasmine know that he does not let his opponent an easy time, but Jasmie admits she learned a lot from this battle. Kenny confesses to Dawn if he wins the next battle against Ash, he wants her to come with him on a journey. Dawn is surprised, while Kenny runs, leaving her in thoughts. Jasmine asks Flint if he let's the opponent have the first move on purpose. Flint confirms, as he wants to see his opponent's moves first and defending, while he can later launch an attack, if his opponent is not strong. Jasmine knows he must be talking about Cynthia, so Ash asks if he plans to challenge her. Flint confirms that as well, but not before he trains as hard as he can. Kenny challenges Ash to a battle; while Ash agrees to, he is hungry - Brock advises they could go to the Center to eat some food. Kenny (grudgingly) accepts and goes. As they get out of the restaurant, the children see Flint and wants autographs. Dawn seems troubled and Jasmine asks what is on her mind. Dawn explains that she can now cheer for Ash, but does not know what to do after the League. Jasmine knows what is she feeling and gives her advice: she must decide on her own what should she do next, in her own interest. As Kenny hears this, Brock asks him what is true secret of love. Kenny is not interested, so Brock lets him know that he needs to put his heart on the line until it gets broken several times. Hearing this, Kenny thanks him for this advice.
After signing the autographs, Flint is asked by Ash how he felt when he won the League. Flint recalls that he battled a very tough opponent, as his Monferno had trouble hitting his opponent's Snorlax. Ash asks what happened next; Flint responds he won not by force or strategy, but by will. He advises Ash that he needs to focus on his wish to win the League, not on how his opponent strong is. Meanwhile, Kenny trains Empoleon, who uses Hydro Cannon. Ash sees him and goes to train as well, sending Buizel for training. Buizel uses SonicBoom on a tree, but gets deflected on Empoleon, but Empoleon repels it on Buizel. Buizel and Empoleon want a battle; Ash and Kenny promise to each other they will use them. Next day, they send their Pokémon, as promised. Empoleon starts with Flash Cannon, but misses. Empoleon follows with Drill Peck, but Buizel intercepts the move. Dawn sees Ash is using a bit of Flint's battle style. Empoleon uses Hydro Cannon and Buizel uses Water Gun to stop, but fails and gets hit. Empoleon goes to use Metal Claw, but Buizel evades and uses Ice Punch. Empoleon dodges and hits it using Metal Claw. Buizel uses Ice Punch, but misses and gets hit by Drill Peck. Buizel is defeated and Kenny wins.
Brock knows that this was a good training and says to Ash that overconfidence can be an enemy. Kenny says to Dawn he will be waiting at the lighthouse, should she want to come with him. Jasmine has decided to go back to the Gym, armed with knowledge she learned. Flint has decided to challenge Cynthia now and though he did not believe that he can defeat her, he is confident about that now. Jasmine and Flint wave goodbye to Ash, Brock and Dawn, as they leave Sunyshore City. Kenny sees the boat is leaving, but sees Dawn left a note. He reads that she goes to cheer for Ash and although she wants to become a Top Coordinator, she believes they will meet each other someday. Kenny sees Dawn on the ship and promise to each other they will do their best to pursue their dreams. Team Rocket follows the ship in their submarine, as they still long for catching Pikachu.
This is the final appearance of Kenny.
- Flint's Monferno has blue eyes instead of black, when it hit Snorlax.
- When Buizel was sent out in the battle, its lips did not move, but said its name.