Encountering a wild Ursaring, Ash's Turtwig attempted to attack it by gnawing on its head. Ursaring shook Turtwig away and chased after it and Ash. Pikachu used Iron Tail and Turtwig fired Razor Leaf, to inflict damage to Ursaring, who retaliated with Hyper Beam. As the heroes ran away from Ursaring, Paul used his Chimchar's Flame Wheel to defeat and capture it. As Team Rocket stole his Chimchar, Paul sent Ursaring. The latter fired Hyper Beam at their balloon, blasting them away and getting his Chimchar back. Ash later reminded Paul about this event when the latter started to criticize Ash's training, for Ash even had teamed up with Paul's brother, Reggie. Before the next round of Hearthome City's Tag Battle tournament, Paul sent all of his Pokémon to attack Chimchar to train it, with Ursaring using Focus Blast. It later went to use Hammer Arm, which Chimchar evaded.
Paul used Ursaring to battle Ash's Chimchar. It deflected Flamethrower, with Focus Punch. As Chimchar went to use Dig, it was thrown out of the ground when Ursaring used Hammer Arm on the floor. It also countered Chimcar's Flame Wheel, before executing Secret Power, hitting Chimchar and frightening it. When Ursaring used Hammer Arm on Chimchar, the latter activated Blaze. When Ursaring used Focus Blast, Ash's Chimchar countered Focus Blast with Flame Wheel and finished Ursaring with a single hit. This battle was remembered by Ash, Dawn and Brock, as they were going to Snowpoint City. Ursaring was used to battle Pyramid King Brandon, where it battled his Regice. The two sides collided using Hammer Arm and Focus Punch. As Ursaring went to execute Focus Blast, it was struck by Regice's Zap Cannon. Brandon then recalled Regice and sent Regirock, who used Stone Edge to defeat Ursaring.
During Ash and Paul's first six on six battle, Ursaring was used to battle Buizel, negating its Water Gun with Hammer Arm, then used Bulk Up to strengthen itself. Buizel used an Aqua Jet, striking Ursaring, whose Slash hurt Buizel, too. Ursaring tossed a Focus Blast, which Buizel redirected back to Ursaring with Aqua Jet. Buizel fired a Sonic Boom to strike Ursaring, who charged with Hammer Arm and struck Buizel. Buizel continued with Aqua Jet, but was defeated with Focus Blast. Ash sent Staraptor next, who used Aerial Ace to dodge Hammer Arm and strike Ursaring. Ursaring retaliated with another Focus Blast, striking Staraptor. Staraptor went to execute Close Combat, but was defeated by Ursaring's Slash and Hammer Arm combo.
At this point, Paul called Ursaring back, and sent it later to battle Pikachu. Pikachu used Quick Attack, but was blown away by Hammer Arm. Pikachu went to use Iron Tail, to which Ursaring attempted to use Focus Blast. However, Ursaring was paralyzed by Pikachu's Static and was struck by Iron Tail. While Pikachu still took damage from being burned by Paul's Magmortar, Ursaring's Guts Ability was triggered. Pikachu went to use Thunderbolt, to which Ursaring took him and tossed him into the lake, defeating Pikachu. Ash sent Chimchar next, whose Flame Wheel dealt a blow on Ursaring. Ursaring went to use Slash, but was stopped by Flamethrower. Chimchar used Dig, and stroke Ursaring before it used Hammer Arm on the ground. Using another Flamethrower, Chimchar defeated Ursaring.
Ash later reminiscenced about this battle, thinking Paul's new strategy had worked in his favor. When Barry spoke how his father treated his Pokémon with respect, Ash remembered his battle with Paul and Ursaring. It made him wonder what kind of strength Paul had that earned him the victory. Facing Barry's Empoleon, Paul swapped his Magmortar with Ursaring. The latter took damage, as Spikes move was used on the battlefield. Barry swapped his Empoleon with Hitmonlee, using its Mega Kick to attack Ursaring, who before used Bulk Up. Ursaring used Hammer Arm, but missed. Hitmonlee was behind a rock, to which Ursaring slashed it to attack Hitmonlee. Hitmonlee quickly used Close Combat to strike Ursaring, pushing it away.
Inflicting damage, Ursaring used Hammer Arm to strike Hitmonlee, but was hit by its Jump Kick. Ursaring fired a Focus Blast, to which Hitmonlee hid behind a rock, but was nevertheless pushed away. Ursaring went to use Hammer Arm, but was burned by Hitmonlee's Blaze Kick. At this point, Ursaring's Guts Ability was activated, pushing Hitmonlee away with Hammer Arm and defeating it. Barry sent Empoleon next, who evaded Ursaring's Slash and hit it with Drill Peck. It then reflected back Ursaring's Focus Blast, so Paul swapped Ursaring with Electivire.
Ursaring was reseen at the end of Ash and Paul's battle in the Sinnoh League with Torterra, Weavile, Honchkrow, Reggie's Staraptor, and Reggie's Swalot. Reggie informed them of Paul's loss, but they were happy to hear that Paul would spend more time training them through battles.
- ^ DP006: Different Strokes For Different Blokes!
- ^ DP040: Top-Down Training!
- ^ DP100: Aiding the Enemy!
- ^ DP051: Glory Blaze!
- ^ DP081: Chim - Charred!
- ^ DP120: Mysterious Creatures: Pokémon!
- ^ DP128: A Pyramiding Rage!
- ^ DP132: Evolving Strategies!
- ^ DP133: Uncrushing Defeat!
- ^ DP141: Challenging a Towering Figure!
- ^ DP184: Casting a Paul on Barry!
- ^ DP188: Battling a Thaw in Relations!