diff --git a/synapse/storage/databases/main/stream.py b/synapse/storage/databases/main/stream.py
index 257c5584d0..cd708e1c99 100644
--- a/synapse/storage/databases/main/stream.py
+++ b/synapse/storage/databases/main/stream.py
@@ -211,44 +211,50 @@ def _make_generic_sql_bound(
 
 
 def _filter_results(
-    direction: str,
-    from_token: Optional[RoomStreamToken],
-    to_token: Optional[RoomStreamToken],
+    lower_token: Optional[RoomStreamToken],
+    upper_token: Optional[RoomStreamToken],
     instance_name: str,
+    topological_ordering: int,
     stream_ordering: int,
 ) -> bool:
-    """Filter results from fetching events in the DB against the given tokens.
+    """Returns True if the event persisted by the given instance at the given
+    topological/stream_ordering falls between the two tokens (taking a None
+    token to mean unbounded).
 
-    This is necessary to handle the case where the tokens include position
-    maps, which we handle by fetching more than necessary from the DB and then
-    filtering (rather than attempting to construct a complicated SQL query).
+    Used to filter results from fetching events in the DB against the given
+    tokens. This is necessary to handle the case where the tokens include
+    position maps, which we handle by fetching more than necessary from the DB
+    and then filtering (rather than attempting to construct a complicated SQL
+    query).
     """
 
-    # We will have already filtered by the topological tokens, so we don't
-    # bother checking topological token bounds again.
-    if from_token and from_token.topological:
-        from_token = None
+    event_historical_tuple = (
+        topological_ordering,
+        stream_ordering,
+    )
 
-    if to_token and to_token.topological:
-        to_token = None
+    if lower_token:
+        if lower_token.topological:
+            # If these are historical tokens we compare the `(topological, stream)`
+            # tuples.
+            if event_historical_tuple <= lower_token.as_historical_tuple():
+                return False
 
-    lower_bound = None
-    if direction == "f" and from_token:
-        lower_bound = from_token.get_stream_pos_for_instance(instance_name)
-    elif direction == "b" and to_token:
-        lower_bound = to_token.get_stream_pos_for_instance(instance_name)
+        else:
+            # If these are live tokens we compare the stream ordering against the
+            # writers stream position.
+            if stream_ordering <= lower_token.get_stream_pos_for_instance(
+                instance_name
+            ):
+                return False
 
-    if lower_bound and stream_ordering <= lower_bound:
-        return False
-
-    upper_bound = None
-    if direction == "b" and from_token:
-        upper_bound = from_token.get_stream_pos_for_instance(instance_name)
-    elif direction == "f" and to_token:
-        upper_bound = to_token.get_stream_pos_for_instance(instance_name)
-
-    if upper_bound and upper_bound < stream_ordering:
-        return False
+    if upper_token:
+        if upper_token.topological:
+            if upper_token.as_historical_tuple() < event_historical_tuple:
+                return False
+        else:
+            if upper_token.get_stream_pos_for_instance(instance_name) < stream_ordering:
+                return False
 
     return True
 
@@ -482,7 +488,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore, metaclass=abc.ABCMeta):
             max_to_id = to_key.get_max_stream_pos()
 
             sql = """
-                SELECT event_id, instance_name, stream_ordering
+                SELECT event_id, instance_name, topological_ordering, stream_ordering
                 FROM events
                 WHERE
                     room_id = ?
@@ -496,9 +502,13 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore, metaclass=abc.ABCMeta):
 
             rows = [
                 _EventDictReturn(event_id, None, stream_ordering)
-                for event_id, instance_name, stream_ordering in txn
+                for event_id, instance_name, topological_ordering, stream_ordering in txn
                 if _filter_results(
-                    "f", from_key, to_key, instance_name, stream_ordering
+                    from_key,
+                    to_key,
+                    instance_name,
+                    topological_ordering,
+                    stream_ordering,
                 )
             ][:limit]
             return rows
@@ -543,7 +553,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore, metaclass=abc.ABCMeta):
             max_to_id = to_key.get_max_stream_pos()
 
             sql = """
-                SELECT m.event_id, instance_name, stream_ordering
+                SELECT m.event_id, instance_name, topological_ordering, stream_ordering
                 FROM events AS e, room_memberships AS m
                 WHERE e.event_id = m.event_id
                     AND m.user_id = ?
@@ -554,9 +564,13 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore, metaclass=abc.ABCMeta):
 
             rows = [
                 _EventDictReturn(event_id, None, stream_ordering)
-                for event_id, instance_name, stream_ordering in txn
+                for event_id, instance_name, topological_ordering, stream_ordering in txn
                 if _filter_results(
-                    "f", from_key, to_key, instance_name, stream_ordering
+                    from_key,
+                    to_key,
+                    instance_name,
+                    topological_ordering,
+                    stream_ordering,
                 )
             ]
 
@@ -1159,7 +1173,11 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore, metaclass=abc.ABCMeta):
             _EventDictReturn(event_id, topological_ordering, stream_ordering)
             for event_id, instance_name, topological_ordering, stream_ordering in txn
             if _filter_results(
-                direction, from_token, to_token, instance_name, stream_ordering
+                lower_token=to_token if direction == "b" else from_token,
+                upper_token=from_token if direction == "b" else to_token,
+                instance_name=instance_name,
+                topological_ordering=topological_ordering,
+                stream_ordering=stream_ordering,
             )
         ][:limit]