diff --git a/spark/v4.0/spark/src/main/java/org/apache/iceberg/spark/actions/RewriteTablePathSparkAction.java b/spark/v4.0/spark/src/main/java/org/apache/iceberg/spark/actions/RewriteTablePathSparkAction.java
index d6a13bcd515d..8fff9ce41df2 100644
--- a/spark/v4.0/spark/src/main/java/org/apache/iceberg/spark/actions/RewriteTablePathSparkAction.java
+++ b/spark/v4.0/spark/src/main/java/org/apache/iceberg/spark/actions/RewriteTablePathSparkAction.java
@@ -72,6 +72,7 @@
 import org.apache.iceberg.relocated.com.google.common.collect.Sets;
 import org.apache.iceberg.spark.JobGroupInfo;
 import org.apache.iceberg.spark.source.SerializableTableWithSize;
+import org.apache.iceberg.util.DeleteFileSet;
 import org.apache.iceberg.util.Pair;
 import org.apache.spark.api.java.function.ForeachFunction;
 import org.apache.spark.api.java.function.MapFunction;
@@ -297,11 +298,22 @@ private Result rebuildMetadata() {
         rewriteManifests(deltaSnapshots, endMetadata, rewriteManifestListResult.toRewrite());
 
     // rebuild position delete files
-    Set<DeleteFile> deleteFiles =
+    // Use DeleteFileSet to ensure proper equality comparison based on file location, content
+    // offset,
+    // and content size. This is particularly important for deletion vectors (DV files) where
+    // multiple DV entries can reference the same Puffin file but have different offsets and sizes.
+    List<ContentFile<?>> allDeleteFiles =
         rewriteManifestResult.toRewrite().stream()
             .filter(e -> e instanceof DeleteFile)
+            .collect(Collectors.toList());
+    Set<DeleteFile> deleteFiles =
+        allDeleteFiles.stream()
             .map(e -> (DeleteFile) e)
-            .collect(Collectors.toSet());
+            .collect(Collectors.toCollection(DeleteFileSet::create));
+    LOG.debug(
+        "Delete files before deduplication: {}, after deduplication with DeleteFileSet: {}",
+        allDeleteFiles.size(),
+        deleteFiles.size());
     rewritePositionDeletes(deleteFiles);
 
     ImmutableRewriteTablePath.Result.Builder builder =
diff --git a/spark/v4.0/spark/src/test/java/org/apache/iceberg/spark/actions/TestRewriteTablePathsAction.java b/spark/v4.0/spark/src/test/java/org/apache/iceberg/spark/actions/TestRewriteTablePathsAction.java
index 0bcaf0af6581..3432a10fee23 100644
--- a/spark/v4.0/spark/src/test/java/org/apache/iceberg/spark/actions/TestRewriteTablePathsAction.java
+++ b/spark/v4.0/spark/src/test/java/org/apache/iceberg/spark/actions/TestRewriteTablePathsAction.java
@@ -565,6 +565,91 @@ public void testPositionDeletesAcrossFiles() throws Exception {
         .isEmpty();
   }
 
+  /**
+   * Test for https://github.com/apache/iceberg/issues/14814
+   *
+   * <p>This test verifies that rewrite_table_path correctly handles position delete files when
+   * multiple snapshots exist. The fix uses DeleteFileSet to properly deduplicate delete files based
+   * on file location, content offset, and content size, rather than relying on object identity.
+   *
+   * <p>Note: The original bug occurred when the same delete file appeared in multiple manifest
+   * entries (e.g., with ADDED and DELETED status), causing AlreadyExistsException. This test
+   * exercises the code path with DeleteFileSet deduplication but may not fully reproduce the edge
+   * case that occurs in production environments with complex manifest structures.
+   */
+  @TestTemplate
+  public void testPositionDeletesWithMultipleSnapshots() throws Exception {
+    // Format versions 3 and 4 use Deletion Vectors stored in Puffin files, which have different
+    // validation rules that prevent adding multiple position deletes for the same data file
+    assumeThat(formatVersion)
+        .as("Format versions 3+ use DVs with different validation rules")
+        .isEqualTo(2);
+
+    Table tableWithPosDeletes =
+        createTableWithSnapshots(
+            tableDir.toFile().toURI().toString().concat("tableWithMultipleSnapshots"),
+            2,
+            Map.of(TableProperties.DELETE_DEFAULT_FILE_FORMAT, "parquet"));
+
+    // Get a data file to create position deletes for
+    DataFile dataFile =
+        tableWithPosDeletes
+            .currentSnapshot()
+            .addedDataFiles(tableWithPosDeletes.io())
+            .iterator()
+            .next();
+
+    // Create first position delete file
+    List<Pair<CharSequence, Long>> deletes1 = Lists.newArrayList(Pair.of(dataFile.location(), 0L));
+    File file1 =
+        new File(
+            removePrefix(tableWithPosDeletes.location() + "/data/deeply/nested/deletes_1.parquet"));
+    DeleteFile positionDeletes1 =
+        FileHelpers.writeDeleteFile(
+                tableWithPosDeletes,
+                tableWithPosDeletes.io().newOutputFile(file1.toURI().toString()),
+                deletes1,
+                formatVersion)
+            .first();
+    tableWithPosDeletes.newRowDelta().addDeletes(positionDeletes1).commit();
+    long snapshot1 = tableWithPosDeletes.currentSnapshot().snapshotId();
+
+    // Create second position delete file
+    List<Pair<CharSequence, Long>> deletes2 = Lists.newArrayList(Pair.of(dataFile.location(), 1L));
+    File file2 =
+        new File(
+            removePrefix(tableWithPosDeletes.location() + "/data/deeply/nested/deletes_2.parquet"));
+    DeleteFile positionDeletes2 =
+        FileHelpers.writeDeleteFile(
+                tableWithPosDeletes,
+                tableWithPosDeletes.io().newOutputFile(file2.toURI().toString()),
+                deletes2,
+                formatVersion)
+            .first();
+    tableWithPosDeletes.newRowDelta().addDeletes(positionDeletes2).commit();
+    long snapshot2 = tableWithPosDeletes.currentSnapshot().snapshotId();
+
+    // Create tags on different snapshots (simulating the production scenario)
+    tableWithPosDeletes.manageSnapshots().createTag("tag1", snapshot1).commit();
+    tableWithPosDeletes.manageSnapshots().createTag("tag2", snapshot2).commit();
+
+    // This should NOT throw AlreadyExistsException
+    RewriteTablePath.Result result =
+        actions()
+            .rewriteTablePath(tableWithPosDeletes)
+            .stagingLocation(stagingLocation())
+            .rewriteLocationPrefix(tableWithPosDeletes.location(), targetTableLocation())
+            .execute();
+
+    // Verify the rewrite completed successfully - should have rewritten 2 delete files
+    assertThat(result.rewrittenDeleteFilePathsCount())
+        .as("Should have rewritten exactly 2 delete files")
+        .isEqualTo(2);
+
+    // Copy the metadata files and data files
+    copyTableFiles(result);
+  }
+
   @TestTemplate
   public void testEqualityDeletes() throws Exception {
     Table sourceTable = createTableWithSnapshots(newTableLocation(), 1);