diff --git a/backend/services/data-management-service/src/main/java/com/datamate/datamanagement/application/DatasetFileApplicationService.java b/backend/services/data-management-service/src/main/java/com/datamate/datamanagement/application/DatasetFileApplicationService.java
index 869a174..8852a15 100644
--- a/backend/services/data-management-service/src/main/java/com/datamate/datamanagement/application/DatasetFileApplicationService.java
+++ b/backend/services/data-management-service/src/main/java/com/datamate/datamanagement/application/DatasetFileApplicationService.java
@@ -575,30 +575,95 @@ public class DatasetFileApplicationService {
         return file;
     }
 
-    /**
-     * 删除文件
-     */
+    /**
+     * 删除文件
+     */
     @Transactional
     public void deleteDatasetFile(String datasetId, String fileId) {
         DatasetFile file = getDatasetFile(datasetId, fileId);
-        Dataset dataset = datasetRepository.getById(datasetId);
-        datasetFileRepository.removeById(fileId);
-        if (!isArchivedStatus(file)) {
-            dataset.setFiles(new ArrayList<>(Collections.singleton(file)));
-            dataset.removeFile(file);
-            datasetRepository.updateById(dataset);
+        if (file == null) {
+            log.warn("File not found: datasetId={}, fileId={}", datasetId, fileId);
+            return;
         }
-        datasetFilePreviewService.deletePreviewFileQuietly(datasetId, fileId);
-        // 删除文件时，上传到数据集中的文件会同时删除数据库中的记录和文件系统中的文件，归集过来的文件仅删除数据库中的记录
-        if (file.getFilePath().startsWith(dataset.getPath())) {
+        String logicalPath = file.getLogicalPath();
+        
+        List<DatasetFile> allVersions = datasetFileRepository.findAllByDatasetIdAndLogicalPath(datasetId, logicalPath);
+        
+        for (DatasetFile versionFile : allVersions) {
+            deleteDatasetFileInternal(datasetId, versionFile);
+        }
+    }
+
+    private void deleteDatasetFileInternal(String datasetId, DatasetFile file) {
+        Dataset dataset = datasetRepository.getById(datasetId);
+        if (file == null || dataset == null) {
+            return;
+        }
+
+        if (isSourceDocument(file)) {
+            deleteDerivedTextFileQuietly(datasetId, file.getId());
+        }
+
+        try {
+            datasetFileRepository.removeById(file.getId());
+        } catch (Exception e) {
+            log.error("Failed to delete file record from database: fileId={}", file.getId(), e);
+        }
+
+        if (!isArchivedStatus(file)) {
+            try {
+                dataset.setFiles(new ArrayList<>(Collections.singleton(file)));
+                dataset.removeFile(file);
+                datasetRepository.updateById(dataset);
+            } catch (Exception e) {
+                log.error("Failed to update dataset: datasetId={}", datasetId, e);
+            }
+        }
+
+        datasetFilePreviewService.deletePreviewFileQuietly(datasetId, file.getId());
+
+        if (file.getFilePath() != null && file.getFilePath().startsWith(dataset.getPath())) {
             try {
                 Path filePath = Paths.get(file.getFilePath());
                 Files.deleteIfExists(filePath);
-            } catch (IOException ex) {
-                throw BusinessException.of(SystemErrorCode.FILE_SYSTEM_ERROR);
-            }
-        }
-    }
+            } catch (IOException ex) {
+                log.error("Failed to delete physical file: filePath={}", file.getFilePath(), ex);
+            }
+        }
+    }
+
+    private void deleteDerivedTextFileQuietly(String datasetId, String sourceFileId) {
+        if (sourceFileId == null || sourceFileId.isBlank()) {
+            return;
+        }
+
+        try {
+            List<DatasetFile> derivedFiles = datasetFileRepository.findAllByDatasetId(datasetId).stream()
+                .filter(f -> isDerivedFileFromSource(f, sourceFileId))
+                .toList();
+
+            for (DatasetFile derivedFile : derivedFiles) {
+                deleteDatasetFileInternal(datasetId, derivedFile);
+            }
+        } catch (Exception e) {
+            log.error("Failed to delete derived text files for sourceFileId: {}", sourceFileId, e);
+        }
+    }
+
+    private boolean isDerivedFileFromSource(DatasetFile file, String sourceFileId) {
+        if (file == null || file.getMetadata() == null || file.getMetadata().isBlank()) {
+            return false;
+        }
+        try {
+            ObjectMapper mapper = new ObjectMapper();
+            Map<String, Object> metadataMap = mapper.readValue(file.getMetadata(), new TypeReference<Map<String, Object>>() {});
+            Object derivedFromFileId = metadataMap.get(DERIVED_METADATA_KEY);
+            return derivedFromFileId != null && sourceFileId.equals(String.valueOf(derivedFromFileId));
+        } catch (Exception e) {
+            log.debug("Failed to parse metadata for derived detection: fileId={}", file.getId(), e);
+            return false;
+        }
+    }
 
     /**
      * 下载文件
diff --git a/backend/services/data-management-service/src/main/java/com/datamate/datamanagement/infrastructure/persistence/mapper/DatasetFileMapper.java b/backend/services/data-management-service/src/main/java/com/datamate/datamanagement/infrastructure/persistence/mapper/DatasetFileMapper.java
index d55c6cc..62a6b95 100644
--- a/backend/services/data-management-service/src/main/java/com/datamate/datamanagement/infrastructure/persistence/mapper/DatasetFileMapper.java
+++ b/backend/services/data-management-service/src/main/java/com/datamate/datamanagement/infrastructure/persistence/mapper/DatasetFileMapper.java
@@ -46,4 +46,13 @@ public interface DatasetFileMapper extends BaseMapper<DatasetFile> {
      * @return 文件数统计列表
      */
     List<DatasetFileCount> countNonDerivedByDatasetIds(@Param("datasetIds") List<String> datasetIds);
+
+    /**
+     * 查询指定逻辑路径的所有文件（包括所有状态）
+     *
+     * @param datasetId 数据集ID
+     * @param logicalPath 逻辑路径
+     * @return 文件列表
+     */
+    List<DatasetFile> findAllByDatasetIdAndLogicalPath(@Param("datasetId") String datasetId, @Param("logicalPath") String logicalPath);
 }
diff --git a/backend/services/data-management-service/src/main/java/com/datamate/datamanagement/infrastructure/persistence/repository/DatasetFileRepository.java b/backend/services/data-management-service/src/main/java/com/datamate/datamanagement/infrastructure/persistence/repository/DatasetFileRepository.java
index 5d50fd6..75bb7f1 100644
--- a/backend/services/data-management-service/src/main/java/com/datamate/datamanagement/infrastructure/persistence/repository/DatasetFileRepository.java
+++ b/backend/services/data-management-service/src/main/java/com/datamate/datamanagement/infrastructure/persistence/repository/DatasetFileRepository.java
@@ -37,6 +37,15 @@ public interface DatasetFileRepository extends IRepository<DatasetFile> {
      */
     DatasetFile findLatestByDatasetIdAndLogicalPath(String datasetId, String logicalPath);
 
+    /**
+     * 查询指定逻辑路径的所有文件（包括所有状态）
+     *
+     * @param datasetId 数据集ID
+     * @param logicalPath 逻辑路径
+     * @return 文件列表
+     */
+    List<DatasetFile> findAllByDatasetIdAndLogicalPath(String datasetId, String logicalPath);
+
     IPage<DatasetFile> findByCriteria(String datasetId, String fileType, String status, String name,
                                       Boolean hasAnnotation, IPage<DatasetFile> page);
 
diff --git a/backend/services/data-management-service/src/main/java/com/datamate/datamanagement/infrastructure/persistence/repository/impl/DatasetFileRepositoryImpl.java b/backend/services/data-management-service/src/main/java/com/datamate/datamanagement/infrastructure/persistence/repository/impl/DatasetFileRepositoryImpl.java
index db68750..0af1c33 100644
--- a/backend/services/data-management-service/src/main/java/com/datamate/datamanagement/infrastructure/persistence/repository/impl/DatasetFileRepositoryImpl.java
+++ b/backend/services/data-management-service/src/main/java/com/datamate/datamanagement/infrastructure/persistence/repository/impl/DatasetFileRepositoryImpl.java
@@ -84,6 +84,11 @@ public class DatasetFileRepositoryImpl extends CrudRepository<DatasetFileMapper,
             .last("LIMIT 1"));
     }
 
+    @Override
+    public List<DatasetFile> findAllByDatasetIdAndLogicalPath(String datasetId, String logicalPath) {
+        return datasetFileMapper.findAllByDatasetIdAndLogicalPath(datasetId, logicalPath);
+    }
+
     public IPage<DatasetFile> findByCriteria(String datasetId, String fileType, String status, String name,
                                              Boolean hasAnnotation, IPage<DatasetFile> page) {
         LambdaQueryWrapper<DatasetFile> wrapper = new LambdaQueryWrapper<DatasetFile>()
diff --git a/backend/services/data-management-service/src/main/resources/mappers/DatasetFileMapper.xml b/backend/services/data-management-service/src/main/resources/mappers/DatasetFileMapper.xml
index ef3ccb5..ede5679 100644
--- a/backend/services/data-management-service/src/main/resources/mappers/DatasetFileMapper.xml
+++ b/backend/services/data-management-service/src/main/resources/mappers/DatasetFileMapper.xml
@@ -64,7 +64,7 @@
           AND (status IS NULL OR status &lt;&gt; 'ARCHIVED')
     </select>
 
-  <select id="findByDatasetIdAndFileName" resultType="com.datamate.datamanagement.domain.model.dataset.DatasetFile">
+   <select id="findByDatasetIdAndFileName" resultType="com.datamate.datamanagement.domain.model.dataset.DatasetFile">
         SELECT <include refid="Base_Column_List"/>
         FROM t_dm_dataset_files
         WHERE dataset_id = #{datasetId}
@@ -74,8 +74,16 @@
         LIMIT 1
     </select>
 
-  <select id="findAllByDatasetId" parameterType="string"
-          resultType="com.datamate.datamanagement.domain.model.dataset.DatasetFile">
+   <select id="findAllByDatasetIdAndLogicalPath" resultType="com.datamate.datamanagement.domain.model.dataset.DatasetFile">
+        SELECT <include refid="Base_Column_List"/>
+        FROM t_dm_dataset_files
+        WHERE dataset_id = #{datasetId}
+          AND logical_path = #{logicalPath}
+        ORDER BY version DESC, upload_time DESC
+    </select>
+
+   <select id="findAllByDatasetId" parameterType="string"
+           resultType="com.datamate.datamanagement.domain.model.dataset.DatasetFile">
         SELECT <include refid="Base_Column_List"/>
         FROM t_dm_dataset_files
         WHERE dataset_id = #{datasetId}