"O'er The Rampardos We Watched"
Dawn dresses in a cheerleading outfit and cheers for Ash. Ash notices this and, with a grin on his face, remarks, "Geez, thanks Dawn."
"Settling a Not-So-Old Score!"
Ash calms Dawn's nerves after she makes what she thought had been a bad appeal and consoles her through the use of Dawn's frequent catchphrase, "No need to worry!". While do so, Ash expresses an encouraging look.
"A Maze-ing Race!"
After Paul tells Ash that he has not seen either Brock or Dawn, Ash wonders if his friends have gotten lost in the maze. He then imagines Dawn yelling "No need to worry!" while being binded by an Onyx and immediately yells out "That's when I worry the most!".
"Tag! We're It...!"
Ash enrolls Dawn in the Hearthome Tag Battle Tournament in an effort to cheer her up following a recent Contest loss. Informed of this, Dawn objects on the basis that she won't do well, but Ash counters with his belief that she will do great and asks her to simply try her best. Dawn agrees, and Ash, with a big grin on his face, raises his hand to to give her a high-five.
Ash showing emotion over Dawn's second Contest
Ash is deeply saddened when Dawn loses in the appeal round for the second time. After the loss, "Jessalina" walks up to her and tells her to leave. Dawn refuses, telling "Jessalina" that she wants to stay, while the camera focuses on Dawn's slightly shaking fist. The camera then cuts to Ash's face. The brown in Ash's eyes can be seen; this usually happens only when Ash is very upset. Ash lowers his head and hides his eyes behind his hat.
Ash credits the training Buizel underwent with Dawn while still in her possession for his recent earning of a badge from Maylene. Dawn blushes and replies, "Thanks, but it was all worth it to see an amazing battle between you and Maylene, Ash." Ash smiles widely at her.
"Cream of the Croagunk Crop!"
Ash asks Dawn to dance during the Croagunk Festival.
"Hungry for the Good Life!"
Ash and Dawn climb onto Team Rocket's robot, but Ash falls off. As he does so, Ash yells Dawn's name twice, once while falling and again after losing sight of her.
"Fighting Fear With Fear!"
Dawn infuriates Ash by suggesting that Ash treat his Pokémon as Gary does. Some PearlShippers consider that to be jealousy over Dawn's supposed feelings for Gary.
"Arriving in Style!"
Dawn becomes frustrated while designing outfits for the collection. Ash assures her that all of her designs are good and tells her to just do her best.
"Camping It Up!"
When Brock comments on how great Conway is with his Venonat, Ash begins to worry and yells, "'Kay Dawn, hang in there!" Later, Ash is happy to see Dawn win the prize for being closest to her Pokémon.
"A Breed Stampede!"
Dawn's Piloswine, hungry for more Poffins, charges her. Ash quickly responds, saving her from injury by placing his arm around her waist and pushing her to safety.
"Another One Gabites the Dust!"
Ursula insults Dawn, angering her. Dawn prepares a retort but Ash beats her to the punch, yelling to Ursula that Dawn is a much better Coordinator and Trainer than she is.
"Trials and Adulations!"
Ash discovers that Dawn has fallen into the river and thus becomes worried. He continues to express concern over her well-being until she is found. Meanwhile, Brock does not show nearly as much concern.
Dawn puts on a show for Ash and his Pokémon, but Ash does not know why. Nurse Joy informs him that it Dawn is trying to cheer up not only his Pokémon but him as well. Ash quickly gives Dawn a weird look as if to say, "Is this true?" Dawn responds with a smile and a wink and starts the show. Ash and his Pokémon enjoy themselves.
"An Egg Scramble!"
When Lyra invites Dawn to battle with her Chikorita, Ash exclaims, "Yeah, go Dawn!" and pushes her to the podium by the shoulder.
"A Rivalry to Gible On!"
Lyra tries to play matchmaker with Dawn and Khoury as the target couple. Later, Ash and friends are separated by a flock of Zubat while exploring a cave. Dawn is shown alone and scared with her Piplup, but, soon after, Ash is shown running up to her and calling out her name.
"Dressed for Jess Success!"
In this episode, Ash states Dawn is awesome and "number one."
"Yes in Dee Dee, It's Dawn!"
In this episode, Ash is seen giving Dawn many kind gestures. First, after Dawn faints, Ash gives her some warm milk to make her feel better—though it is revealed Brock told Ash to go get it—and comments on how worried he is about her well-being. These kind words touch Dawn, prompting her to note that he is being really, almost uncharacteristically, nice to her. Later, during the Contest, Brock worries aloud that Dawn's performance might not go well; Ash objects and tells Brock that he thinks Dawn will be fine. Finally, after the first round of the Contest, Ash runs into the contestant area (Brock behind), telling Dawn that she was awesome and complimenting her Pokémon pair. Dawn is touched and she and Ash high-five. At the episode's end, Ursula comments on how close Ash and Dawn have become.
"Dawn of a Royal Day!"
Dawn tries on a princess outfit leaving Ash with a visibly stunned face (though some say it's because she looks so much like Princess Salvia). Ash praises Dawn, commenting that the dress looks good on her.
"Memories are Made of Bliss!"
Throughout the episode, Ash was constantly joking around with Dawn. Some PearlShippers think that this was his way of making the goodbye not as heartbreaking. At the beginning of the episode, Ash tells Dawn's mother that traveling with Dawn was a lot of fun and that he enjoyed her around. At the end of the episode, Ash becomes worried about Dawn when she was crying as he left so he yells her catchphrase and cheers her up.