diff --git a/src/main/kotlin/controller/api/AudioApiController.kt b/src/main/kotlin/controller/api/AudioApiController.kt
index fe26b9f..6530669 100644
--- a/src/main/kotlin/controller/api/AudioApiController.kt
+++ b/src/main/kotlin/controller/api/AudioApiController.kt
@@ -22,7 +22,6 @@
         private const val PAGE_LIMIT = 50
     }
 
-    // TODO 複数キーワード対応
     @GetMapping
     fun getAudioList(
         @RequestParam("audio", required = false) audioName: String?,
@@ -48,7 +47,7 @@
     fun updateHistory(
         @PathVariable("slug") slug: String
     ): ResponseEntity<Void> {
-        audioService.updateHistory(slug)
+        audioService.updateHistory(slug, PAGE_LIMIT)
         return ResponseEntity.ok(null)
     }
 
@@ -60,4 +59,12 @@
         audioService.update(slug, request)
         return ResponseEntity.ok(null)
     }
+
+    @DeleteMapping("{slug}")
+    fun deleteAudio(
+        @PathVariable("slug") slug: String
+    ): ResponseEntity<Void> {
+        audioService.delete(slug)
+        return ResponseEntity.ok(null)
+    }
 }
\ No newline at end of file
diff --git a/src/main/kotlin/dao/AlbumDao.kt b/src/main/kotlin/dao/AlbumDao.kt
index c8fcdcc..fa12669 100644
--- a/src/main/kotlin/dao/AlbumDao.kt
+++ b/src/main/kotlin/dao/AlbumDao.kt
@@ -47,6 +47,9 @@
     @UpdateProvider(type = Sql::class, method = "updateOne")
     fun updateOne(@Param("entity") entity: AlbumEntity)
 
+    @Delete("DELETE FROM album WHERE id = #{id}")
+    fun deleteOneById(@Param("id") id: Long): Boolean
+
     class Sql {
         companion object {
             @JvmStatic
diff --git a/src/main/kotlin/dao/AudioDao.kt b/src/main/kotlin/dao/AudioDao.kt
index 1214fd4..654dd5d 100644
--- a/src/main/kotlin/dao/AudioDao.kt
+++ b/src/main/kotlin/dao/AudioDao.kt
@@ -54,6 +54,9 @@
     @UpdateProvider(type = Sql::class, method = "updateOne")
     fun updateOne(@Param("entity") entity: AudioEntity)
 
+    @Delete("DELETE FROM audio WHERE slug = #{slug}")
+    fun deleteOneBySlug(@Param("slug") slug: String): Boolean
+
     class Sql {
         companion object {
             @JvmStatic
diff --git a/src/main/kotlin/dao/AudioPlayHistoryDao.kt b/src/main/kotlin/dao/AudioPlayHistoryDao.kt
index d535a84..d8ad53c 100644
--- a/src/main/kotlin/dao/AudioPlayHistoryDao.kt
+++ b/src/main/kotlin/dao/AudioPlayHistoryDao.kt
@@ -5,7 +5,10 @@
 package net.piedpiper.bremer.dao
 
 import net.piedpiper.bremer.entity.AudioPlayHistoryEntity
+import net.piedpiper.bremer.utils.SelectSQLBuilder
+import net.piedpiper.bremer.utils.WHERE_IN
 import org.apache.ibatis.annotations.*
+import org.apache.ibatis.jdbc.SQL
 import org.springframework.stereotype.Repository
 
 @Repository("bremer.dao.AudioPlayHistoryDao")
@@ -13,8 +16,14 @@
 interface AudioPlayHistoryDao {
 
     @ResultMap("net.piedpiper.bremer.AudioPlayHistoryEntity")
-    @Select("SELECT * FROM audio_play_history ORDER BY last_played_at DESC LIMIT #{limit}")
-    fun findAllOrderLastPlayedAtDescLimit(@Param("limit") limit: Int): List<AudioPlayHistoryEntity>
+    @Select(
+        "SELECT * FROM audio_play_history ORDER BY last_played_at DESC " +
+                "LIMIT #{limit} OFFSET #{offset}"
+    )
+    fun findAllOrderLastPlayedAtDescLimit(
+        @Param("limit") limit: Int,
+        @Param("offset") offset: Long
+    ): List<AudioPlayHistoryEntity>
 
     @Insert(
         """
@@ -25,4 +34,17 @@
     )
     @Options(useGeneratedKeys = true, keyProperty = "id")
     fun insertOrUpdateOne(@Param("entity") entity: AudioPlayHistoryEntity): Boolean
+
+    @DeleteProvider(type = Sql::class, method = "deleteAllByIds")
+    fun deleteAllByIds(@Param("ids") ids: List<Long>): Long
+
+    class Sql {
+        companion object {
+            @JvmStatic
+            fun deleteAllByIds(@Param("ids") ids: List<Long>): String = SQL()
+                .DELETE_FROM("audio_play_history")
+                .WHERE_IN("id", "ids", ids.size)
+                .toString()
+        }
+    }
 }
\ No newline at end of file
diff --git a/src/main/kotlin/dao/PlaylistDao.kt b/src/main/kotlin/dao/PlaylistDao.kt
index c616ec7..01d9e0a 100644
--- a/src/main/kotlin/dao/PlaylistDao.kt
+++ b/src/main/kotlin/dao/PlaylistDao.kt
@@ -36,7 +36,7 @@
     fun insertOne(@Param("entity") entity: PlaylistEntity): Boolean
 
     @Delete("DELETE FROM playlist WHERE slug = #{slug}")
-    fun deleteBySlug(@Param("slug") slug: String): Boolean
+    fun deleteOneBySlug(@Param("slug") slug: String): Boolean
 
     @UpdateProvider(type = Sql::class, method = "updateOne")
     fun updateOne(@Param("entity") entity: PlaylistEntity)
diff --git a/src/main/kotlin/service/AudioService.kt b/src/main/kotlin/service/AudioService.kt
index 0fcbdd7..9d28abf 100644
--- a/src/main/kotlin/service/AudioService.kt
+++ b/src/main/kotlin/service/AudioService.kt
@@ -74,7 +74,7 @@
     /** 最近再生した曲一覧を取得 */
     @Transactional
     fun getLeastRecentlyAccessedAudio(pageSize: Int): AudioListResponse {
-        val historyMap = audioPlayHistoryDao.findAllOrderLastPlayedAtDescLimit(pageSize)
+        val historyMap = audioPlayHistoryDao.findAllOrderLastPlayedAtDescLimit(pageSize, 0L)
             .associateBy { it.audioId }
         return if (historyMap.isNotEmpty())
             audioDao.findAllByIdIn(historyMap.keys.map { it })
@@ -86,6 +86,7 @@
         else AudioListResponse()
     }
 
+    /** 更新 */
     @Transactional
     fun update(slug: String, request: AudioRequest) = audioDao.findOneBySlugWithLock(slug)
         ?.let {
@@ -107,14 +108,37 @@
             }
         } ?: throw NotFoundException()
 
-    fun updateHistory(slug: String) {
-        audioDao.findOneBySlug(slug)?.let {
+    /** 音楽削除 */
+    @Transactional
+    fun delete(slug: String) = audioDao.findOneBySlugWithLock(slug)
+        ?.let {
+            audioDao.deleteOneBySlug(it.slug)
+            if (audioDao.findAllByAlbumIdIn(listOf(it.albumId))
+                    .isEmpty()
+            ) {
+                albumDao.deleteOneById(it.albumId);
+            }
+        } ?: throw NotFoundException()
+
+    /** 履歴更新 */
+    @Transactional
+    fun updateHistory(slug: String, pageSize: Int) {
+        audioDao.findOneBySlug(slug)?.let { it ->
             audioPlayHistoryDao.insertOrUpdateOne(
                 AudioPlayHistoryEntity(
                     audioId = it.id,
                     lastPlayedAt = LocalDateTime.now(ZoneId.of("Asia/Tokyo"))
                 )
             )
+            while (true) {
+                audioPlayHistoryDao.findAllOrderLastPlayedAtDescLimit(pageSize, 1L)
+                    ?.let { result ->
+                        if (result.isEmpty()) {
+                            return
+                        }
+                        audioPlayHistoryDao.deleteAllByIds(result.map { history -> history.id })
+                    }
+            }
         }
     }
 
@@ -133,13 +157,19 @@
         return audioDao.findAllByAlbumIdIn(albums.map { it.id }.distinct())
     }
 
-    private fun findAllByAlbumNamesLikeLimit(albumNamesLike: List<String>, limit: Int): List<AudioEntity> {
+    private fun findAllByAlbumNamesLikeLimit(
+        albumNamesLike: List<String>,
+        limit: Int
+    ): List<AudioEntity> {
         val albums = albumDao.findAllByNamesLikeLimit(albumNamesLike, limit)
         return if (albums.isNotEmpty()) audioDao
             .findAllByAlbumIdIn(albums.map { it.id }) else emptyList()
     }
 
-    private fun findAllByTagNamesLikeLimit(tagNamesLike: List<String>, limit: Int): List<AudioEntity> {
+    private fun findAllByTagNamesLikeLimit(
+        tagNamesLike: List<String>,
+        limit: Int
+    ): List<AudioEntity> {
         val tags = tagDao.findAllByNamesLikeLimit(tagNamesLike, limit)
         return if (tags.isNotEmpty()) audioDao.findAllByTagIdIn(tags.map { it.id }) else emptyList()
     }
diff --git a/src/main/kotlin/service/PlaylistService.kt b/src/main/kotlin/service/PlaylistService.kt
index ce5ef04..5bd58b7 100644
--- a/src/main/kotlin/service/PlaylistService.kt
+++ b/src/main/kotlin/service/PlaylistService.kt
@@ -89,7 +89,7 @@
             playlistAudioDao.deleteAllByIds(
                 playlist.playlistAudio.map { it.id })
         }
-        playlistDao.deleteBySlug(slug)
+        playlistDao.deleteOneBySlug(slug)
     }
 
     @Transactional