Ash and his friends had gotten lost in Bewilder Forest in Different Strokes for Different Blokes. While looking for a way out, they encountered an angry Ursaring, which started chasing them. After getting out of the forest, the group encountered Paul. Using his Chimchar, Paul weakened Ursaring and captured it. Paul used his Pokédex to scan its attacks, and then decided to keep it.
Ursaring was again seen in Top-Down Training! where Paul used it to save Chimchar from Team Rocket. It next appeared in Glory Blaze! where Paul used it in training Chimchar.
Ursaring was next used in Chim - Charred! where it was used in a battle against Ash's Chimchar. With its brute strength and power, it almost defeated Chimchar but after Chimchar lost control of its Ability, Blaze, it defeated Ursaring.
Ursaring was used against Brandon's Regice in A Pyramiding Rage!. After a clash of its Hammer Arm and Regice's Focus Punch, it attacked Ursaring with Zap Cannon which paralyzed it. Brandon then recalled Regice and sent out Regirock. Paul gave up on Ursaring and did not command it to attack. It then got knocked out by Regirock's Stone Edge.
In Evolving Strategies! Ursaring was used in the Full Battle between Paul and Ash. With a Bulk Up, it easily defeated Ash's Buizel and Staraptor before being recalled. During the battle with Pikachu, it was paralyzed by Pikachu's Static. However this in turn activated its Guts Ability which caused Ursaring to gain extra power which ultimately led to Pikachu's defeat. Ursaring was eventually brought down by Chimchar once again.
In Casting a Paul on Barry!, Ursaring was used to fight against Barry's Empoleon, but Barry replaced Empoleon with his Hitmonlee. During a very close match between the two, Ursaring was burned by Hitmonlee's Blaze Kick, activating Ursaring's Guts Ability again, giving Ursaring enough power to defeat Hitmonlee. It then fought against Barry's Empoleon again, but after having a Focus Blast fired back to it, Paul recalled it.
Ursaring appeared briefly again in Battling a Thaw in Relations! at Reggie's house along with Paul's Torterra, Weavile, and Honchkrow.