Ep. 100: Ash and friends relax on an island while Team Rocket plots to steal the Pokémon
Aired on May 27, 1999Filler

100
Ash, his friends, and their Pokémon decide to take a break on a nearby island to relax and get better acquainted. However, Team Rocket has other plans for the Pokémon and intend to steal them.
Episodes
- Ep. 96 · Ash travels to the Grapefruit Islands to stop a grapefruit-eating Snorlax with Jigglypuff's help.
- Ep. 97 · Ash and friends pursue Team Rocket to a haunted ship for a lost trophy
- Ep. 98 · Meowth arrives on an island where locals worship him as the Great Meowth of Bounty
- Ep. 99 · Tracey discovers a wounded Scyther on Murcott Island and learns it lost its leadership role.
- Ep. 100 · Ash and friends relax on an island while Team Rocket plots to steal the Pokémon
- Ep. 101 · Ash faces Elite Four member Prima on Mandarin Island after a winning streak
- Ep. 102 · Ash and friends encounter rival trainers interfering with two Nidoran's romance in Victorian Town.
- Ep. 103 · Ash helps deliver Magnemite to power an island town
- Ep. 104 · Ash and friends investigate a troublesome monster in Trovitopolis sewers