diff --git a/src/discord/queue.py b/src/discord/queue.py
index a2794ed..f1a0907 100644
--- a/src/discord/queue.py
+++ b/src/discord/queue.py
@@ -50,10 +50,9 @@ class MessageQueue:
 
 	def delete_all_with_matching_metadata(self, **properties):
 		"""Deletes all of the messages that have matching metadata properties (useful for message redaction)"""
-		for message in messagequeue:
-			if self.compare_message_to_dict(message[1], properties):
-				# TODO Delete messages from the queue
-				raise NotImplemented
+		for index, item in reversed(list(enumerate(self._queue))):
+			if self.compare_message_to_dict(item[1], properties):
+				self._queue.pop(index)
 
 	def resend_msgs(self):
 		if self._queue:
diff --git a/src/fileio/database.py b/src/fileio/database.py
index 4593f00..99126f9 100644
--- a/src/fileio/database.py
+++ b/src/fileio/database.py
@@ -52,12 +52,12 @@ def add_entry(pageid: int, revid: int, logid: int, message):
 def clean_entries():
 	"""Cleans entries that are 50+"""
 	cleanup = db_cursor.execute(
-		"SELECT message_id FROM messages WHERE message_id NOT IN (SELECT message_id FROM messages ORDER BY message_id asc LIMIT 50);")
+		"SELECT message_id FROM messages WHERE message_id NOT IN (SELECT message_id FROM messages ORDER BY message_id desc LIMIT 50);")
 	for row in cleanup:
-		db_cursor.execute("DELETE FROM messages WHERE message_id = ?", (cleanup[0]))
-	cleanup = db_cursor.execute("SELECT msg_id FROM event WHERE msg_id NOT IN (SELECT msg_id FROM event ORDER BY msg_id asc LIMIT 50);")
+		db_cursor.execute("DELETE FROM messages WHERE message_id = ?", (row[0]))
+	cleanup = db_cursor.execute("SELECT msg_id FROM event WHERE msg_id NOT IN (SELECT msg_id FROM event ORDER BY msg_id desc LIMIT 50);")
 	for row in cleanup:
-		db_cursor.execute("DELETE FROM event WHERE msg_id = ?", (cleanup[0]))
+		db_cursor.execute("DELETE FROM event WHERE msg_id = ?", (row[0]))
 	db_connection.commit()
 
 db_connection, db_cursor = create_connection()