In the Diamond & Pearl series, Ash appeared with another new outfit, consisting of a black vest, white undershirt, new jeans, new sneakers, and his hat's Poké Ball is blue.
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Season 10: Diamond and Pearl
Departing for Sinnoh, Ash once again left his previous captures at Professor Oak's laboratory, with the exception of his Aipom who'd snuck along. After arriving in Sinnoh by boat and reuniting with Brock, he gained yet another new traveling companion in Dawn, a confident girl interested in following in her mother's footsteps as a Pokemon Coordinator. After receiving new clothes from his mother in the mail, Ash gained a new rival in a Trainer named Paul. Later in the season, Ash misses meeting Team Galactic due to moving on with his journey too soon. He won his first two Sinnoh Gym Badges: a Coal Badge from Roark and a Forest Badge from Gardenia. Ash encountered J, who temporarily kidnapped Pikachu by turning it into stone. Ash's first Sinnoh capture was a Starly which evolved into Staravia, and a Turtwig. His final Sinnoh acquisition came when he adopted Paul's Chimchar by the end of the season.
Season 11: DP Battle Dimension
In this season, Ash continued battling and earning badges while Dawn continued to earn contest ribbons. They also encountered Team Galactic and tried to stop them from stealing the Adamant Orb. During this time, Ash earns his fifth Gym Badge. For most of the season, Ash had to wait for Gym Leader Fantina to return to her Gym in order to challenge her. Ash reunited with May during the Wallace Cup and took part as a coordinator once again (per Hoenn Pokémon League Champion Wallace's request). Late one night with Pikachu, he saw the spirit of Azelf rise out of the lake the contest was being held at. He tied with Maylene but earned a Cobble Badge from her and defeated both Crasher Wake and Fantina for the Fen and Relic Badges. He also acquired a new rival in Barry, a somewhat clumsy boy who insists on fining people. Ash acquired a few more Pokemon during this season; at the suggestion of Zoey, he traded his Aipom for Dawn's Buizel, the only trade so far he hasn't reversed; his Turtwig evolved into Grotle; and he caught a Gligar which became a Gliscor.
Season 12: DP Galactic Battles
Continuing his journey in Sinnoh, Ash managed to beat Byron, winning the Mine Badge and Candice, winning the Icicle Badge. After his victory over Candice at the Snowpoint Gym, Ash briefly reunited with Brandon from the Battle Pyramid back in Kanto's Battle Frontier and witnessed a full Six on Six battle between him and his rival Paul. It was then after that battle that it was Ash's turn for his full battle with Paul which occured at Lake Acuity. However, Ash was not victorious in his battle with Paul even after Chimchar evolved into Monferno. Along the trip to Sunyshore City, Ash and his friends encounter International Policeman Looker and were recruited to help stop the plans of Team Galactic as the three of them were chosen to share a bond with the three Lake Spirit Pokémon, during which Brock managed to find Uxie. Managing to find Team Galactic in the middle of creating a new universe with the captive Lake Trio controlling Palkia and Dialga, Ash, Dawn and Brock freed the trio and Team Galactic was arrested while their leader vanished into the collapsing new world, effectively disbanding Team Galactic. At the end of the season, Ash gives Gliscor to the Air Battle Master named McCann for some training and has caught himself a Gible which was learning Draco Meteor.
Season 13: DP Sinnoh League Victors
After the Team Galactic incident, Ash entered the Sinnoh League after beating Volkner and earning the Beacon Badge. He also reunited with Jasmine from the Olivine Gym before heading to Lily Of the Valley. Taking a different approach in this League than he did in Hoenn, Ash combined his previous captures with his current Pokemon to form well-balanced teams of new and old. The Sinnoh League was one of the hardest and most intense Leagues he ever competed in, as he had rivals Paul and Barry to compete with, and a mysterious trainer who joined with the Legendary PokémonDarkrai. He battled against most of his rivals save for Barry, who battled Paul and lost, so Ash's next match was against Paul.
The battle was intense as Paul showed Pokémon that he didn't normally use while Ash had reassembled his team of six from their earlier battle at Lake Acuity. The fight came down to Paul's Electivire and Ash's Infernape. Despite taking heavy damage, Infernape won the match for Ash with its ability Blaze. After defeating Paul, Ash faced an opponent other Trainers in the League dreaded to face as he was hard to defeat: the Trainer with the Darkrai, Tobias. After losing three of his Pokemon to it, Ash was able to defeat Tobias' Darkrai with Sceptile and even knocked out Tobias' Latios with Pikachu. However, as the rest of Ash's Pokémon had fainted, he lost the match and was eliminated. To this day, the Sinnoh League remains Ash's most impressive performance in a Pokémon League Tournament: he reached the Top 4 - the farthest he'd ever gotten in any Pokémon League - and was the only one of Tobias' opponents to defeat two of his Pokémon, let alone his Darkrai. After the Sinnoh League, Ash bade farewell to Dawn as she wished to continue entering contests, and also parted ways with Brock, his oldest friend and longest-running traveling companion for the final time, as Brock now wished to become a Pokémon Doctor.
Ash was given Pikachu by Professor Oak as the original Kanto starter Pokemon had been taken. Originally, Pikachu would not listen to Ash and constantly shocked him. However, after accidentally angering a flock of Spearow, Pikachu had a change of heart when he saw Ash defend him. Since then, Pikachu has assisted and been very successful in many of Ash's wins and over time has adopted Ash's mannerisms. Pikachu does not want to be in his Poké Ball so he stays out all the time, often riding on Ash's shoulder or head.
Ash's Staraptor evolved from Staravia during a PokéRinger contest against Paul's Honchkrow. As it has evolved, it became one of the powerhouses of Ash's team and was still used for long-distance searching.
After being knocked to the brink of fainting in a battle against Barry's Empoleon, Monferno went berserk with his Blaze Ability and unleashed his full power against Team Rocket. While protecting the Pokémon, he evolved into Infernape. He was later used in a battle against Flint's Infernape, but lost due to his lack of experience.
Originally captured by Dawn, Buizel has always been an incredibly strong Pokémon with an aptitude for Pokémon Battles. After Zoey saw how Ash & Dawn had Pokémon that preferred the other's vocations, a trade followed.
During its Gligar stage, Gliscor was a fairly weak Pokémon, not knowing many attacks and thus not being very strong, all due to its level. However, it evolved by grabbing a Razor Fang while he was falling, he gained a lot of strength and confidence. Even after evolving though, it still wished to battle more and still vied for Ash's approval. During a battle with the Air Battle Master, it learned Giga Impact but decided to stay for training. But during Sinnoh League, it returned back to Ash with powerful moves from its training. However instead of returning to the Air Battle Master, Gliscor decided to be with Ash and stay at Professor Oak's Lab.
Ash first encountered his Gible when he met Old Lady Tatsu, a woman who was teaching an Altaria a special move for Dragon Pokémon, Draco Meteor. Ash assisted Gible in the learning of the move and Gible decided to follow Ash. He also has the habit of biting on to heads. Later on, Ash noticed Gible followed him and eventually captured him. He had lots of trouble with Draco Meteor at first, often hitting poor Piplup on his head.
Captured in the Orange Islands when stealing all the fruit from a small Island range, Snorlax has become a major powerhouse of Ash's, when it is awake that is. Due to its massive feeding requirements, Ash felt it better to stay at Professor Oak's, however it is still used for a number of Gym, League & Frontier battles. Also, Snorlax had defeated a Medicham, even at a Fighting disadvantage.
Heracross was the first Pokémon that Ash captured in Johto. It loves tree sap and has been known to suck the pollen out of Bulbasaur's Bulb on several occasions causing Bulbasaur to be annoyed. It is a powerful Pokémon of Ash's and has been used in several Gym, League, Frontier battles and even the Sinnoh Pokémon League.
While training for the Sinnoh League, Ash brought his Cyndaquil with many of his other Pokémon. However, Team Rocket tried to cause problems and Cyndaquil evolved in order to stop them. Quilava has numerous powerful attacks such as Flame Wheel at its disposal, showing that it has completely overcome its previous hindrances in its base form and is sure to be a powerful Pokémon within Ash's team.
After rejoining Ash's team as a Phanpy, it evolved to help protect Pikachu from Team Rocket. However even after the evolution, it kept its playful personality from being a Phanpy which sometimes can cause mayhem with other younger Pokémon.
After evolving from Grovyle to defend its love interest, it lost all its ability to use attacks due to a broken heart caused by rejection. Eventually regaining the ability to use the attacks, Sceptile became a vital powerhouse in Ash's team which can hold his own against legendary Pokémon including Deoxys, Regirock, and Darkrai. Despite being one of Ash's best-trained Pokémon, Ash decided to leave Sceptile at Oak's Lab while he travelled to Sinnoh. Sceptile was used again to defeat a Darkrai in the Sinnoh Pokémon League.
Aipom originally met Ash on a mountain where she worshiped a Giant Slaking, where she stole Ash's hat. However after Ash found Aipom, they quickly befriended. Ash originally was going to give the hat to Aipom but she gave it back. For a short time Aipom followed Ash and turned up at the Grand Festival, again stealing Ash's hat. Near to the finals of the Grand Festival, Ash decided to battle Aipom and finally caught her. Apart from her battling strengths, Aipom has shown a great aptitude for Contests and as such, was eventually traded to Dawn for her Contests and few episodes later Aipom evolved into Ambipom.
Ash befriended Giratina after he saved it from Zero. They both worked together to stop Zero from taking over the Reverse World. It later helped Dialga and Palkia protect Ash and his friends from Arceus's attacks and buy them time to change the timeline for the better.
Ash first encountered Azelf in its spirit form at Lake Valor. When Azelf was captured by Team Galactic, Ash and Pikachu came and freed it from the Red Chain's power. Together with their hearts connected along with Dawn, Mesprit, Brock, and Uxie, Ash and Azelf worked together to calm Dialga and Palkia and save the Sinnoh region from destruction.