diff --git a/src/ytdl_sub/downloaders/downloader.py b/src/ytdl_sub/downloaders/downloader.py
index a2509ee7..4f2c31b3 100644
--- a/src/ytdl_sub/downloaders/downloader.py
+++ b/src/ytdl_sub/downloaders/downloader.py
@@ -33,7 +33,9 @@ from ytdl_sub.entries.base_entry import BaseEntry
 from ytdl_sub.entries.entry import Entry
 from ytdl_sub.entries.entry_parent import EntryParent
 from ytdl_sub.entries.variables.kwargs import PLAYLIST_ENTRY
+from ytdl_sub.entries.variables.kwargs import REQUESTED_SUBTITLES
 from ytdl_sub.entries.variables.kwargs import SOURCE_ENTRY
+from ytdl_sub.entries.variables.kwargs import UPLOAD_DATE_INDEX
 from ytdl_sub.thread.log_entries_downloaded_listener import LogEntriesDownloadedListener
 from ytdl_sub.utils.exceptions import FileNotDownloadedException
 from ytdl_sub.utils.file_handler import FileHandler
@@ -382,9 +384,18 @@ class Downloader(DownloadArchiver, Generic[DownloaderOptionsT], ABC):
             ytdl_options_overrides={"writeinfojson": False, "skip_download": self.is_dry_run},
         )
 
-        # Workaround for the ytdlp issue
-        # pylint: disable=protected-access
-        entry._kwargs["requested_subtitles"] = download_entry_dict.get("requested_subtitles")
+        upload_date_idx = self._enhanced_download_archive.mapping.get_num_entries_with_upload_date(
+            upload_date_standardized=entry.upload_date_standardized
+        )
+
+        entry.add_kwargs(
+            {
+                # Workaround for the yt-dlp issue that does not include subs in playlist downloads
+                REQUESTED_SUBTITLES: download_entry_dict.get(REQUESTED_SUBTITLES),
+                # Tracks number of entries with the same upload date to make them unique
+                UPLOAD_DATE_INDEX: upload_date_idx,
+            }
+        )
         # pylint: enable=protected-access
 
         return entry
diff --git a/src/ytdl_sub/entries/variables/entry_variables.py b/src/ytdl_sub/entries/variables/entry_variables.py
index a37a7eb2..5f537710 100644
--- a/src/ytdl_sub/entries/variables/entry_variables.py
+++ b/src/ytdl_sub/entries/variables/entry_variables.py
@@ -26,6 +26,7 @@ from ytdl_sub.entries.variables.kwargs import SOURCE_UPLOADER
 from ytdl_sub.entries.variables.kwargs import SOURCE_UPLOADER_ID
 from ytdl_sub.entries.variables.kwargs import SOURCE_UPLOADER_URL
 from ytdl_sub.entries.variables.kwargs import SOURCE_WEBPAGE_URL
+from ytdl_sub.entries.variables.kwargs import UPLOAD_DATE_INDEX
 
 # This file contains mixins to a BaseEntry subclass. Ignore pylint's "no kwargs member" suggestion
 # pylint: disable=no-member
@@ -376,6 +377,46 @@ class EntryVariables(BaseEntryVariables):
         """
         return "jpg"
 
+    @property
+    def upload_date_index(self: Self) -> int:
+        """
+        Returns
+        -------
+        int
+            The i'th entry downloaded with this upload date.
+        """
+        return self.kwargs_get(UPLOAD_DATE_INDEX, 0) + 1
+
+    @property
+    def upload_date_index_padded(self: Self) -> str:
+        """
+        Returns
+        -------
+        int
+            The upload_date_index padded two digits
+        """
+        return _pad(self.upload_date_index, 2)
+
+    @property
+    def upload_date_index_reversed(self: Self) -> int:
+        """
+        Returns
+        -------
+        int
+            100 - upload_date_index
+        """
+        return 100 - self.upload_date_index
+
+    @property
+    def upload_date_index_reversed_padded(self: Self) -> str:
+        """
+        Returns
+        -------
+        int
+            The upload_date_index padded two digits
+        """
+        return _pad(self.upload_date_index_reversed, 2)
+
     @property
     def upload_date(self: Self) -> str:
         """
diff --git a/src/ytdl_sub/entries/variables/kwargs.py b/src/ytdl_sub/entries/variables/kwargs.py
index 80304ca2..ec1d14cf 100644
--- a/src/ytdl_sub/entries/variables/kwargs.py
+++ b/src/ytdl_sub/entries/variables/kwargs.py
@@ -40,6 +40,8 @@ PLAYLIST_UPLOADER = _("playlist_uploader")
 PLAYLIST_UPLOADER_ID = _("playlist_uploader_id")
 PLAYLIST_UPLOADER_URL = _("playlist_uploader_url")
 
+UPLOAD_DATE_INDEX = _("upload_date_index", backend=True)
+REQUESTED_SUBTITLES = _("requested_subtitles", backend=True)
 UID = _("id")
 EXTRACTOR = _("extractor")
 EPOCH = _("epoch")
diff --git a/src/ytdl_sub/ytdl_additions/enhanced_download_archive.py b/src/ytdl_sub/ytdl_additions/enhanced_download_archive.py
index a995983f..dcb10bbb 100644
--- a/src/ytdl_sub/ytdl_additions/enhanced_download_archive.py
+++ b/src/ytdl_sub/ytdl_additions/enhanced_download_archive.py
@@ -227,6 +227,21 @@ class DownloadMappings:
             del self._entry_mappings[entry_id]
         return self
 
+    def get_num_entries_with_upload_date(self, upload_date_standardized: str) -> int:
+        """
+        Parameters
+        ----------
+        upload_date_standardized
+            A standardized upload date
+
+        Returns
+        -------
+        Number of entries in the mapping with this upload date
+        """
+        return len(
+            [_ for _ in self._entry_mappings.values() if _.upload_date == upload_date_standardized]
+        )
+
     def get_entries_out_of_range(self, date_range: DateRange) -> Dict[str, DownloadMapping]:
         """
         Parameters
diff --git a/tests/unit/entries/conftest.py b/tests/unit/entries/conftest.py
index 8be3a8b1..91411446 100644
--- a/tests/unit/entries/conftest.py
+++ b/tests/unit/entries/conftest.py
@@ -75,6 +75,10 @@ def mock_entry_to_dict(
         "uploader": "abc123",
         "uploader_id": "abc123",
         "uploader_url": "https://yourname.here",
+        "upload_date_index": 1,
+        "upload_date_index_padded": "01",
+        "upload_date_index_reversed": 99,
+        "upload_date_index_reversed_padded": "99",
         "upload_date": upload_date,
         "upload_date_standardized": "2021-01-12",
         "upload_year": 2021,