diff --git a/django/contrib/admin/views/main.py b/django/contrib/admin/views/main.py
index 2f0e915d5e..e587d4ffca 100644
--- a/django/contrib/admin/views/main.py
+++ b/django/contrib/admin/views/main.py
@@ -308,7 +308,12 @@ class ChangeList:
                     order_field = self.get_ordering_field(field_name)
                     if not order_field:
                         continue  # No 'admin_order_field', skip it
-                    if hasattr(order_field, 'as_sql'):
+                    if isinstance(order_field, OrderBy):
+                        if pfx == '-':
+                            order_field = order_field.copy()
+                            order_field.reverse_ordering()
+                        ordering.append(order_field)
+                    elif hasattr(order_field, 'resolve_expression'):
                         # order_field is an expression.
                         ordering.append(order_field.desc() if pfx == '-' else order_field.asc())
                     # reverse order if order_field has already "-" as prefix
diff --git a/tests/admin_views/admin.py b/tests/admin_views/admin.py
index 6a11d5b9bb..bf10151356 100644
--- a/tests/admin_views/admin.py
+++ b/tests/admin_views/admin.py
@@ -105,6 +105,7 @@ class ArticleAdmin(admin.ModelAdmin):
         'content', 'date', callable_year, 'model_year', 'modeladmin_year',
         'model_year_reversed', 'section', lambda obj: obj.title,
         'order_by_expression', 'model_property_year', 'model_month',
+        'order_by_f_expression', 'order_by_orderby_expression',
     )
     list_editable = ('section',)
     list_filter = ('date', 'section')
@@ -122,12 +123,20 @@ class ArticleAdmin(admin.ModelAdmin):
         })
     )
 
+    # These orderings aren't particularly useful but show that expressions can
+    # be used for admin_order_field.
     def order_by_expression(self, obj):
         return obj.model_year
-    # This ordering isn't particularly useful but shows that expressions can
-    # be used for admin_order_field.
     order_by_expression.admin_order_field = models.F('date') + datetime.timedelta(days=3)
 
+    def order_by_f_expression(self, obj):
+        return obj.model_year
+    order_by_f_expression.admin_order_field = models.F('date')
+
+    def order_by_orderby_expression(self, obj):
+        return obj.model_year
+    order_by_orderby_expression.admin_order_field = models.F('date').asc(nulls_last=True)
+
     def changelist_view(self, request):
         return super().changelist_view(request, extra_context={'extra_var': 'Hello!'})
 
diff --git a/tests/admin_views/tests.py b/tests/admin_views/tests.py
index e833c44f95..c9ca64097f 100644
--- a/tests/admin_views/tests.py
+++ b/tests/admin_views/tests.py
@@ -364,30 +364,47 @@ class AdminViewBasicTest(AdminViewBasicTestCase):
         )
 
     def test_change_list_sorting_callable_query_expression(self):
-        """
-        Query expressions may be used for admin_order_field. (column 9 is
-        order_by_expression in ArticleAdmin).
-        """
-        response = self.client.get(reverse('admin:admin_views_article_changelist'), {'o': '9'})
-        self.assertContentBefore(
-            response, 'Oldest content', 'Middle content',
-            'Results of sorting on callable are out of order.'
-        )
-        self.assertContentBefore(
-            response, 'Middle content', 'Newest content',
-            'Results of sorting on callable are out of order.'
-        )
+        """Query expressions may be used for admin_order_field."""
+        tests = [
+            ('order_by_expression', 9),
+            ('order_by_f_expression', 12),
+            ('order_by_orderby_expression', 13),
+        ]
+        for admin_order_field, index in tests:
+            with self.subTest(admin_order_field):
+                response = self.client.get(
+                    reverse('admin:admin_views_article_changelist'),
+                    {'o': index},
+                )
+                self.assertContentBefore(
+                    response, 'Oldest content', 'Middle content',
+                    'Results of sorting on callable are out of order.'
+                )
+                self.assertContentBefore(
+                    response, 'Middle content', 'Newest content',
+                    'Results of sorting on callable are out of order.'
+                )
 
     def test_change_list_sorting_callable_query_expression_reverse(self):
-        response = self.client.get(reverse('admin:admin_views_article_changelist'), {'o': '-9'})
-        self.assertContentBefore(
-            response, 'Middle content', 'Oldest content',
-            'Results of sorting on callable are out of order.'
-        )
-        self.assertContentBefore(
-            response, 'Newest content', 'Middle content',
-            'Results of sorting on callable are out of order.'
-        )
+        tests = [
+            ('order_by_expression', -9),
+            ('order_by_f_expression', -12),
+            ('order_by_orderby_expression', -13),
+        ]
+        for admin_order_field, index in tests:
+            with self.subTest(admin_order_field):
+                response = self.client.get(
+                    reverse('admin:admin_views_article_changelist'),
+                    {'o': index},
+                )
+                self.assertContentBefore(
+                    response, 'Middle content', 'Oldest content',
+                    'Results of sorting on callable are out of order.'
+                )
+                self.assertContentBefore(
+                    response, 'Newest content', 'Middle content',
+                    'Results of sorting on callable are out of order.'
+                )
 
     def test_change_list_sorting_model(self):
         """