diff --git a/src/Filter/AbstractDateFilter.php b/src/Filter/AbstractDateFilter.php
index c470ef13f..fc6951dac 100644
--- a/src/Filter/AbstractDateFilter.php
+++ b/src/Filter/AbstractDateFilter.php
@@ -160,7 +160,13 @@ private function filterRange(ProxyQueryInterface $query, string $alias, string $
         $endDateParameterName = $this->getNewParameterName($query);
 
         if (DateRangeOperatorType::TYPE_NOT_BETWEEN === $type) {
-            $this->applyWhere($query, sprintf('%s.%s < :%s OR %s.%s > :%s', $alias, $field, $startDateParameterName, $alias, $field, $endDateParameterName));
+            if (null !== $value['start']) {
+                $this->applyWhere($query, sprintf('%s.%s %s :%s', $alias, $field, '<', $startDateParameterName));
+            }
+
+            if (null !== $value['end']) {
+                $this->applyWhere($query, sprintf('%s.%s %s :%s', $alias, $field, '>', $endDateParameterName));
+            }
         } else {
             if (null !== $value['start']) {
                 $this->applyWhere($query, sprintf('%s.%s %s :%s', $alias, $field, '>=', $startDateParameterName));
diff --git a/tests/Filter/DateTimeRangeFilterTest.php b/tests/Filter/DateTimeRangeFilterTest.php
index 53dafa97a..784128669 100644
--- a/tests/Filter/DateTimeRangeFilterTest.php
+++ b/tests/Filter/DateTimeRangeFilterTest.php
@@ -14,6 +14,7 @@
 namespace Sonata\DoctrineORMAdminBundle\Tests\Filter;
 
 use Sonata\AdminBundle\Filter\Model\FilterData;
+use Sonata\AdminBundle\Form\Type\Operator\DateRangeOperatorType;
 use Sonata\DoctrineORMAdminBundle\Datagrid\ProxyQuery;
 use Sonata\DoctrineORMAdminBundle\Filter\DateTimeRangeFilter;
 use Sonata\Form\Type\DateTimeRangeType;
@@ -43,4 +44,48 @@ public function testGetType(): void
 
         static::assertSame(DateTimeRangeType::class, $filter->getFieldType());
     }
+
+    public function testFilterNotBetweenStartDate(): void
+    {
+        $filter = new DateTimeRangeFilter();
+        $filter->initialize('field_name', ['field_options' => ['class' => 'FooBar']]);
+
+        $proxyQuery = new ProxyQuery($this->createQueryBuilderStub());
+
+        $startDateTime = new \DateTime('2023-10-03T12:00:01');
+
+        $filter->filter($proxyQuery, 'alias', 'field', FilterData::fromArray([
+            'type' => DateRangeOperatorType::TYPE_NOT_BETWEEN,
+            'value' => [
+                'start' => $startDateTime,
+                'end' => null,
+            ],
+        ]));
+
+        self::assertSameQuery(['WHERE alias.field < :field_name_0'], $proxyQuery);
+        self::assertSameQueryParameters(['field_name_0' => $startDateTime], $proxyQuery);
+        static::assertTrue($filter->isActive());
+    }
+
+    public function testFilterNotBetweenEndDate(): void
+    {
+        $filter = new DateTimeRangeFilter();
+        $filter->initialize('field_name', ['field_options' => ['class' => 'FooBar']]);
+
+        $proxyQuery = new ProxyQuery($this->createQueryBuilderStub());
+
+        $endDateTime = new \DateTime('2023-10-03T12:00:01');
+
+        $filter->filter($proxyQuery, 'alias', 'field', FilterData::fromArray([
+            'type' => DateRangeOperatorType::TYPE_NOT_BETWEEN,
+            'value' => [
+                'start' => null,
+                'end' => $endDateTime,
+            ],
+        ]));
+
+        self::assertSameQuery(['WHERE alias.field > :field_name_1'], $proxyQuery);
+        self::assertSameQueryParameters(['field_name_1' => $endDateTime], $proxyQuery);
+        static::assertTrue($filter->isActive());
+    }
 }