Cheren and Hilda are childhood friends. He visits her house on the day that they receive their Pokémon from Professor Juniper along with Bianca. He always chooses the starter that Hilda's starter is weak to. Both have a dream to become the Unova champion and travel around to earn eight badges. Throughout their journey, they run into each other and battle multiple times.
While on their journey, Cheren and Hilda also run into Team Plasma and battle them multiple times. They will also battle on team twice. When Hilda heads to victory road, Cheren battles her one more time in order to determine if she is ready for the Elite Four. When N's Castle appears, he defeats the Elite Four so that he can go help Hilda against Team Plasma. He and Alder take Ghetsis into custody and he later apologizes to her when the Shadow Triad comes to help him escape.
After Unova is saved from Team Plasma, Hilda can find Cheren on Route 5. Afterwards, he will move to Victory Road and they can battle once a day. Hilda eventually leaves Unova in order to search for N. Over the next two years, Cheren becomes the Gym Leader of Aspertia City. If Memory Link is used, he will keep his same team to battle the new player with.
CheckmateShipping is a very popular Pokémon ship. This is due to the fact that they are childhood friends and friendly rivals who start their journey at the same time. Cheren also seems to be somewhat protective of Hilda and makes sure that she is ready to face the Elite Four as well as helping her against Team Plasma. CheckmateShipping is commonly shipped along with RebelShipping because it pairs the four main characters with each other. It commonly rivals ChessShipping, FerrisWheelShipping, and DualRivalShipping.
- The name of the ship refers to the fact that the game is called Pokémon Black and White which are also the colors of chess.
- If Hilbert is chosen as the player character instead of Hilda, then the two will not know each other.