diff --git a/swh/loader/svn/ra.py b/swh/loader/svn/ra.py
--- a/swh/loader/svn/ra.py
+++ b/swh/loader/svn/ra.py
@@ -1,4 +1,4 @@
-# Copyright (C) 2016-2020  The Software Heritage developers
+# Copyright (C) 2016-2021  The Software Heritage developers
 # See the AUTHORS file at the top-level directory of this distribution
 # License: GNU General Public License version 3, or any later version
 # See top-level LICENSE file for more information
@@ -302,8 +302,14 @@
                 shutil.rmtree(fpath)
             else:
                 os.remove(fpath)
-        if path in EOL_STYLE:
-            del EOL_STYLE[path]
+
+        # when deleting a directory ensure to remove any eol style setting for the
+        # file it contains as they can be added again later in another revision
+        # without the svn:eol-style property set
+        fullpath = os.path.join(self.rootpath, path)
+        for eol_path in list(EOL_STYLE):
+            if eol_path.startswith(fullpath):
+                del EOL_STYLE[eol_path]
 
     def update_checksum(self):
         raise NotImplementedError("This should be implemented.")
diff --git a/swh/loader/svn/tests/test_loader.py b/swh/loader/svn/tests/test_loader.py
--- a/swh/loader/svn/tests/test_loader.py
+++ b/swh/loader/svn/tests/test_loader.py
@@ -3,11 +3,13 @@
 # License: GNU General Public License version 3, or any later version
 # See top-level LICENSE file for more information
 
+from io import BytesIO
 import os
 import subprocess
 
 import pytest
-from subvertpy import SubversionException
+from subvertpy import SubversionException, delta, repos
+from subvertpy.ra import Auth, RemoteAccess, get_username_provider
 
 from swh.loader.svn.loader import (
     SvnLoader,
@@ -786,3 +788,73 @@
             "skipped_content": 0,
             "snapshot": 1,
         }
+
+
+def test_loader_eol_style_file_property_handling_edge_case(swh_storage, tmp_path):
+    # create a repository
+    repo_path = os.path.join(tmp_path, "tmprepo")
+    repos.create(repo_path)
+
+    # connect to the "remote" repository using the file transport.
+    repo_url = f"file://{repo_path}"
+    conn = RemoteAccess(repo_url, auth=Auth([get_username_provider()]))
+
+    # first commit
+    with conn.get_commit_editor(
+        {
+            "svn:log": (
+                "Add a directory containing a file with CRLF end of line "
+                "and set svn:eol-style property to native so CRLF will be "
+                "replaced by LF in the file when exporting the revision"
+            )
+        }
+    ) as editor:
+        with editor.open_root() as root:
+            root.add_directory("directory").close()
+            with root.add_file("directory/file_with_crlf_eol.txt") as file:
+                file.change_prop("svn:eol-style", "native")
+                txdelta = file.apply_textdelta()
+                delta.send_stream(BytesIO(b"Hello world!\r\n"), txdelta)
+
+    # second commit
+    with conn.get_commit_editor(
+        {"svn:log": "Remove previously added directory and file"}
+    ) as editor:
+        with editor.open_root() as root:
+            root.delete_entry("directory")
+
+    # third commit
+    with conn.get_commit_editor(
+        {
+            "svn:log": (
+                "Add again same directory containing same file with CRLF end of line "
+                "but do not set svn:eol-style property value so CRLF will not be "
+                "replaced by LF when exporting the revision"
+            )
+        }
+    ) as editor:
+        with editor.open_root() as root:
+            root.add_directory("directory").close()
+            with root.add_file("directory/file_with_crlf_eol.txt") as file:
+                txdelta = file.apply_textdelta()
+                delta.send_stream(BytesIO(b"Hello world!\r\n"), txdelta)
+
+    # instantiate a svn loader checking after each processed revision that
+    # the repository filesystem it reconstructed does not differ from a subversion
+    # export of that revision
+    loader = SvnLoader(
+        swh_storage, repo_url, destination_path=tmp_path, check_revision=1
+    )
+
+    assert loader.load() == {"status": "eventful"}
+    assert loader.visit_status() == "full"
+    assert get_stats(loader.storage) == {
+        "content": 2,
+        "directory": 5,
+        "origin": 1,
+        "origin_visit": 1,
+        "release": 0,
+        "revision": 3,
+        "skipped_content": 0,
+        "snapshot": 1,
+    }