Four Roads Diverged in a Pokémon Port! (Japanese: サトシＶＳケンゴ！それぞれの船出！！Satoshi VS Kengo! Sailing for Respective Roads!!) is the 180th episode of the Diamond & Pearl series, and the 646th episode of the Pokémon anime. It aired in Japan on June 10, 2010 and in the United States on November 6, 2010.
On their way to Lily of the Valley Island, site of the Sinnoh League, Ash, Dawn, and Brock are seen waiting for their ship to come. While waiting they run into Kenny, who has set his goal to the next Grand Festival, was having a special training session with Olivine City's Gym Leader, Jasmine. Kenny tells Dawn how great she was in the Grand Festival and was impressed that she made it all the way to the final round before losing to Zoey. After hearing that, Dawn starts to stress about not making her future goal yet. At that moment, Kenny tells Dawn that if he beats Ash in battle, she has to travel with him.
Suddenly, Team Rocket shows up and takes Kenny's Floatzel until Flint's Infernape saves Floatzel with a powerful Overheat. Jasmine then introduces herself and challenges Flint to a battle. Flint sends out his Infernape and Jasmine sends out Steelix. Dawn scans Steelix with her Pokédex and comments on the type advantage Infernape has, but Ash comments on how Steelix is also Jasmine's strongest Pokémon. Ash then decides to send out his Infernape so that it could watch Flint's Infernape battle and take notes. After a tough battle and because of a type advantage, Flint's Infernape defeats Jasmine's Steelix with a powerful Flare Blitz.
After the battle, Kenny (carrying on with his plan) challenges Ash to a battle, and Ash happily accepts, so the battle is then scheduled to go on for tomorrow. Afterwards, Flint tells Ash about a past battle when his Infernape was still a Monferno and of the time he won the Sinnoh League. Flint also tells Ash that he is training for his upcoming match with Cynthia, and how he was unsure if he was either ready or not. Later on, Ash sees Kenny training his Empoleon, encouraging Ash to train Buizel, but Buizel's SonicBoom is deflected of a tree and then Empoleon deflects it back at Buizel. Because the two Water types are so eager to battle each other, Kenny makes the request for the battle to be Buizel vs. Empoleon, and Ash happily accepts the offer. The next day, the battle Ash against Kenny starts.
Ash sends out Buizel and Kenny sends out Empoleon, much to Dawn's surprise. During the battle Ash uses Flint's battling style and remarks that he wanted to polish Buizel's defense. The battle ends with Buizel losing after taking a direct hit with Drill Peck. After, Flints decided to go ahead and battle Cynthia, and Dawn decided to go cheer for Ash at the Sinnoh League and then start her own journey. Kenny then leaves and continues his own journey.
As of this episode, half of the Johto Gym Leaders have appeared in the Diamond & Pearl series, though Jasmine is the only one who has appeared in person.
Aside from her, only Clair has been seen in her Generation IV outfit, with Whitney and Morty appearing in their Generation II designs. Jasmine is also shown in her Generation II outfit in flashbacks in this episode.
In Flint's flashback in Flint Sparks the Fire!, he shows that his Infernape was still a Chimchar when he grew up. However, his flashback in this episode shows that it had evolved into a Monferno when he was still a kid.
When Kenny's Empoleon used Metal Claw and Buizel used Ice Punch, Empoleon's chest was colored blue.
When Piplup turns around at the ferry station his beak is coloured light blue.
When Ash calls for Infernape to watch the battle, its shoulder pads were white, but in the next scene, they were their original color.