diff --git a/CHANGELOG.md b/CHANGELOG.md
index cbd190d71..09f7bba18 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -18,6 +18,8 @@
 
 ### Server
 - Enhance: エンドポイント`antennas/update`の必須項目を`antennaId`のみに
+- Fix: フォローリクエストを作成する際に既存のものは削除するように  
+  (Cherry-picked from https://activitypub.software/TransFem-org/Sharkey/-/merge_requests/440)
 
 ## 2024.3.1
 
diff --git a/packages/backend/src/core/UserFollowingService.ts b/packages/backend/src/core/UserFollowingService.ts
index 0a492c06e..deeecdeb1 100644
--- a/packages/backend/src/core/UserFollowingService.ts
+++ b/packages/backend/src/core/UserFollowingService.ts
@@ -511,6 +511,12 @@ export class UserFollowingService implements OnModuleInit {
 		if (blocking) throw new Error('blocking');
 		if (blocked) throw new Error('blocked');
 
+		// Remove old follow requests before creating a new one.
+		await this.followRequestsRepository.delete({
+			followeeId: followee.id,
+			followerId: follower.id,
+		});
+
 		const followRequest = await this.followRequestsRepository.insert({
 			id: this.idService.gen(),
 			followerId: follower.id,