On January 28, 2020 GRACE COMPANY opened CHECKMATE's Instagram account and revealed the group's logo. On September 8, their agency confirmed the group would debut on September 21 with the single "Drum". Sometime in early October, all references and photos of member Nason were deleted from the group's social medias and platforms.
On November 4, Haechang was announced as a new member through a live stream on the agency's Instagram, and on November 19, GRACE COMPANY updated the group's description on their website, removing Nason's name from the line-up, and therefore, confirming his departure. On December 10, 2020, the agency confirmed that Nason and their newest member Haechang had left the group due to personal circumstances. On January 20, 2021 GRACE COMPANY announced that CHECKMATE would be coming back with their second single album "You".
On February 15, it was announced that the single's release would be delayed to March 4 for the completion of the album. On March 5, the single was delayed again towards the end of the month. A new version of "Drum" was released the following day as a pre-release single.
On March 19, it was confirmed that the single would be released on March 29. On December 17, CHECKMATE's YouTube channel creator and manager announced that CHECKMATE had disbanded, with the members pursuing individual activities.
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