diff --git a/fastlabel/__init__.py b/fastlabel/__init__.py
index 4b7794a..f071e16 100644
--- a/fastlabel/__init__.py
+++ b/fastlabel/__init__.py
@@ -2308,10 +2308,16 @@ def __export_index_color_image(
                         if count == 0:
                             cv_draw_points = []
                             if utils.is_clockwise(points):
-                                cv_draw_points = self.__get_cv_draw_points(points)
+                                cv_draw_points = self.__get_cv_draw_points(
+                                    utils.sort_segmentation_points(points)
+                                )
                             else:
+                                reverse_points = utils.reverse_points(points)
+                                sorted_points = utils.sort_segmentation_points(
+                                    reverse_points
+                                )
                                 cv_draw_points = self.__get_cv_draw_points(
-                                    utils.reverse_points(points)
+                                    sorted_points
                                 )
                             cv2.fillPoly(
                                 seg_mask_image,
@@ -2323,9 +2329,11 @@ def __export_index_color_image(
                         else:
                             # Reverse hollow points for opencv because these points are
                             # counterclockwise
-                            cv_draw_points = self.__get_cv_draw_points(
-                                utils.reverse_points(points)
+                            reverse_points = utils.reverse_points(points)
+                            sorted_points = utils.sort_segmentation_points(
+                                reverse_points
                             )
+                            cv_draw_points = self.__get_cv_draw_points(sorted_points)
                             cv2.fillPoly(
                                 seg_mask_image,
                                 [cv_draw_points],
@@ -2362,7 +2370,8 @@ def __export_index_color_image(
 
     def __get_cv_draw_points(self, points: List[int]) -> List[int]:
         """
-        Convert points to pillow draw points. Diagonal points are not supported.
+        Convert points to pillow draw points. Diagonal points are not supported
+        Annotation clockwise draw.
         """
         x_points = []
         x_points.append(points[0])
diff --git a/fastlabel/utils.py b/fastlabel/utils.py
index 3ba7d45..ca8d209 100644
--- a/fastlabel/utils.py
+++ b/fastlabel/utils.py
@@ -85,6 +85,31 @@ def reverse_points(points: List[int]) -> List[int]:
     return reversed_points
 
 
+def sort_segmentation_points(points: List[int]) -> List[int]:
+    """
+    e.g.)
+    [1, 2, 1, 1, 2, 1, 2, 2, 1, 2] => [1, 1, 2, 1, 2, 2, 1, 2, 1, 1]
+    """
+    points_array = np.array(points).reshape((-1, 2))[1:]
+    base_point_index = 0
+    points_list = points_array.tolist()
+    for index, val in enumerate(points_list):
+        if index == 0:
+            continue
+        if (
+            val[1] <= points_list[base_point_index][1] and val[0] <= points_list[base_point_index][0]
+        ):
+            base_point_index = index
+    new_points_array = np.vstack(
+        [
+            points_array[base_point_index:],
+            points_array[:base_point_index],
+            np.array([points_array[base_point_index]]),
+        ]
+    )
+    return new_points_array.ravel().tolist()
+
+
 def is_clockwise(points: list) -> bool:
     """
     points: [x1, y1, x2, y2, x3, y3, ... xn, yn]