ContestShipping

Contestshipping is the het ship between May and Drew from the Pokémon fandom.

In Pokémon the Series: Ruby and Sapphire
Drew debuted in Now That's Flower Power!, where he was seen watching May training for the Slateport City Pokémon Contest. He said she needed a lot of practice and insulted her Pokémon, which made her angry. Later, when May and her friends were looking for Bluk Berries, he appeared and challenged her to a battle. He did a good job showing off the attacks of his Roselia, but the battle was interrupted when Team Rocket stole the Bluk Berries. He then helped May to retrieve the Berries and left.

In Come What May!, he competed in the Fallarbor Contest; however, he lost to Grace and her Medicham. Following May's victory, Drew congratulated her by giving her a rose. This gesture was repeated in many other episodes.

In Who, What, When, Where, Wynaut?, it was revealed that Drew had obtained his fifth Ribbon. When May showed him her four Ribbons, he told her that there was only one more Pokémon Contest to be held before the Grand Festival, and criticized her for relying on luck and for not having strategies. May then challenged him to a battle, which was interrupted by Team Rocket's attempt to steal Pikachu. Accidentally, Drew was pulled into Team Rocket's submarine along with the rest of the group. When the submarine exploded, the entire group was blasted into the air. They fell in the Mirage Island, where they met a group of Wynaut.

In Rhapsody in Drew, he faced May in the quarterfinals of the Hoenn Grand Festival. Using his Roselia and Flygon, he was able to defeat May, who was using her Combusken and Skitty.

In Spontaneous Combusken!, when May said she was ready to defeat him in the Chrysanthemum Contest, Drew revealed that he wasn't going to compete because he had participated in several Pokémon Contests lately and his Pokémon were exhausted and in need of some rest and relaxation.

In New Plot, Odd Lot! and Going for Choke!, Drew watched May competing for her fifth and final Ribbon in the Mulberry City Pokémon Contest. He also helped Ash to frustrate Harley's plans of sabotaging May.

Drew reappeared to compete in the Kanto Grand Festival in May, We Harley Drew'd Ya!, where he was reunited with his old friend and rival Solidad, who had defeated him in his very first Pokémon Contest a long time ago. He managed to pass the Appeals Round and quickly reached the quarterfinals, where he found himself against May once again. He fought a hard battle, but his Flygon and Absol ended up being defeated by May's Combusken and Squirtle.

In The Unbeatable Lightness of Seeing!, after finding May feeling down, he decided to have a Contest Battle with her to cheer her up, which he ended up winning. At the end of the episode, he revealed that he would be traveling to the Johto region to participate in Pokémon Contests there.

In Pokémon the Series: Diamond and Pearl
In A Full Course Tag Battle!, it was revealed in a flashback that Drew's Roselia has evolved into a Roserade. May also revealed that Drew was still a major adversary during her journey in Johto.

Drew made cameo appearances with Harley and Solidad in Staging a Heroes' Welcome! and Strategy with a Smile!, where they were at Ecruteak City, watching May live on TV as she competed in the Wallace Cup.

Fanon
Contestshipping is the most popular ship involving May in the Fandom, and also the most popular ship involving Drew. In Fanfiction, this ship is usually paired with Pokeshipping (Ash x Misty), Ikarishipping (Dawn x Paul), and Leafgreenshipping (Leaf x Gary).

In fanon, Drew commonly mocks May by calling her different months, such as June, July, August, instead of May.

Contestshipping's rivals include Advancedshipping, which is the pairing between Ash and May. However, there are no other common ships involving May or Drew in the Fandom.

Fandom
FAN FICTION
 * May/Drew tag on FanFiction.net
 * May/Drew tag on FanFiction.net

Trivia

 * The ship name Contestshipping comes from the fact that May and Drew both commonly compete in Pokémon contests.