diff --git a/app/models/custom_field/order_statements.rb b/app/models/custom_field/order_statements.rb
index 939ad6f57acf..5181381b6b05 100644
--- a/app/models/custom_field/order_statements.rb
+++ b/app/models/custom_field/order_statements.rb
@@ -141,10 +141,18 @@ def order_by_user_sql
   end
 
   def order_by_version_sql
-    <<-SQL
-    (SELECT cv_version.name FROM #{Version.quoted_table_name} cv_version
-     WHERE cv_version.id = #{select_custom_value_as_decimal}
-     LIMIT 1)
+    columns = multi_value? ? "array_agg(cv_version.name ORDER BY cv_version.name)" : "cv_version.name"
+    limit = multi_value? ? "" : "LIMIT 1"
+
+    <<-SQL.squish
+      (
+        SELECT #{columns}
+          FROM #{Version.quoted_table_name} cv_version
+          INNER JOIN #{CustomValue.quoted_table_name} cv_sort
+            ON cv_sort.value IS NOT NULL AND cv_sort.value != '' AND cv_version.id = cv_sort.value::bigint
+          WHERE #{cv_sort_only_custom_field_condition_sql}
+          #{limit}
+      )
     SQL
   end
 
diff --git a/spec/models/queries/projects/project_query_custom_field_order_spec.rb b/spec/models/queries/projects/project_query_custom_field_order_spec.rb
index f3d3dc2a6ca4..800b03b40e2d 100644
--- a/spec/models/queries/projects/project_query_custom_field_order_spec.rb
+++ b/spec/models/queries/projects/project_query_custom_field_order_spec.rb
@@ -332,17 +332,22 @@ def project_without_cf_value
 
         let(:projects) do
           [
-            project_with_cf_value(*id_by_name.fetch_values("10.10.10")),
-            project_with_cf_value(*id_by_name.fetch_values("10.10.2")),
-            # TODO: second version is ignored
-            project_with_cf_value(*id_by_name.fetch_values("9", "10.10.2")),
-            project_with_cf_value(*id_by_name.fetch_values("9", "10.10.10")),
+            project_with_cf_value(*id_by_name.fetch_values("10.10.10")),        # 10.10.10
+            project_with_cf_value(*id_by_name.fetch_values("9", "10.10.10")),   # 10.10.10, 9
+            project_with_cf_value(*id_by_name.fetch_values("10.10.10", "9")),   # 10.10.10, 9
+            project_with_cf_value(*id_by_name.fetch_values("10.10.2")),         # 10.10.2
+            project_with_cf_value(*id_by_name.fetch_values("10.2", "10.10.2")), # 10.10.2, 10.2
+            project_with_cf_value(*id_by_name.fetch_values("10.10.2", "9")),    # 10.10.2, 9
             project # TODO: should be at index 0
           ]
         end
 
-        # TODO: second version is ignored, so order due to falling back on id asc
-        let(:projects_desc) { projects.values_at(4, 2, 3, 1, 0) }
+        let(:projects_desc) do
+          indexes = projects.each_index.to_a
+          # order of values for a work package is ignored, so ordered by falling back on id asc
+          indexes[1...3] = indexes[1...3].reverse
+          projects.values_at(*indexes.reverse)
+        end
       end
     end
   end
diff --git a/spec/models/query/results_cf_sorting_integration_spec.rb b/spec/models/query/results_cf_sorting_integration_spec.rb
index 9edbc8045e2f..50cf643c9a41 100644
--- a/spec/models/query/results_cf_sorting_integration_spec.rb
+++ b/spec/models/query/results_cf_sorting_integration_spec.rb
@@ -324,17 +324,22 @@ def wp_without_cf_value
 
         let(:work_packages) do
           [
-            wp_with_cf_value(id_by_name.fetch_values("10.10.10")),
-            wp_with_cf_value(id_by_name.fetch_values("10.10.2")),
-            # TODO: second version is ignored
-            wp_with_cf_value(id_by_name.fetch_values("9", "10.10.2")),
-            wp_with_cf_value(id_by_name.fetch_values("9", "10.10.10")),
+            wp_with_cf_value(id_by_name.fetch_values("10.10.10")),        # 10.10.10
+            wp_with_cf_value(id_by_name.fetch_values("9", "10.10.10")),   # 10.10.10, 9
+            wp_with_cf_value(id_by_name.fetch_values("10.10.10", "9")),   # 10.10.10, 9
+            wp_with_cf_value(id_by_name.fetch_values("10.10.2")),         # 10.10.2
+            wp_with_cf_value(id_by_name.fetch_values("10.2", "10.10.2")), # 10.10.2, 10.2
+            wp_with_cf_value(id_by_name.fetch_values("10.10.2", "9")),    # 10.10.2, 9
             wp_without_cf_value # TODO: should be at index 0
           ]
         end
 
-        # TODO: second version is ignored, so order due to falling back on id asc
-        let(:work_packages_desc) { work_packages.values_at(4, 2, 3, 1, 0) }
+        let(:work_packages_desc) do
+          indexes = work_packages.each_index.to_a
+          # order of values for a project is ignored, so ordered by falling back on id asc
+          indexes[1...3] = indexes[1...3].reverse
+          work_packages.values_at(*indexes.reverse)
+        end
       end
     end
   end