1Misty and Brock Leave
2Bye Bye Butterfree
3Pikachu and the Other Pokemon Cry After Ash is Turned to Stone
4Charmander is Abandoned by His Trainer
5Ash is Turned to Stone and Brought Back by Pikachu's Tears
6Pickachu's Goodbye
7Pikachu Chooses Ash Over Freedom
8Tommy's Parents Almost Die
9Stoutland Dies
10Goodra Leaves
11Ash Sends Butterfree Off with His Mate
12Pikachu is Turned Into Stone
13Weezing and Arbok Leave
14Ash Loses to Ritchie After Charizard Refuses to Battle
15Ash Says Goodbye to Charizard
16Serena Cries After Failing to Make It Past the First Round of the Pokemon Showcase
18Espurr Drives Off to Grandmother's Gravesite
19Dawn and Brock Leave
21Manaphy Says Goodbye to May
22Pikachu Decides Not to Evolve
23Lucario's Death in Movie 8
27Max Gets Upset Over Norman's Loss to Ash
28Bonnie Says Goodbye to Squishy
29Ash leaves Greninja for Sun and Moon
31Pikachu Almost Dies After Being Attacked by a Flock of Spearows
32When Serena leaves at the end of XY
33Ash yells at Serena because he wanted to be alone (Pokemon XYZ Episode 28)
34Dawn's Piplup Runs Away
35When James left his Chimecho with his grandparents