diff --git a/core/trino-main/src/test/java/io/trino/sql/query/QueryAssertions.java b/core/trino-main/src/test/java/io/trino/sql/query/QueryAssertions.java
index 1d84ac176faf..df402d455f47 100644
--- a/core/trino-main/src/test/java/io/trino/sql/query/QueryAssertions.java
+++ b/core/trino-main/src/test/java/io/trino/sql/query/QueryAssertions.java
@@ -444,7 +444,7 @@ public QueryAssert isFullyPushedDown()
 
             if (!skipResultsCorrectnessCheckForPushdown) {
                 // Compare the results with pushdown disabled, so that explicit matches() call is not needed
-                verifyResultsWithPushdownDisabled();
+                hasCorrectResultsRegardlessOfPushdown();
             }
             return this;
         }
@@ -511,17 +511,19 @@ private QueryAssert hasPlan(PlanMatchPattern expectedPlan, Consumer<Plan> additi
 
             if (!skipResultsCorrectnessCheckForPushdown) {
                 // Compare the results with pushdown disabled, so that explicit matches() call is not needed
-                verifyResultsWithPushdownDisabled();
+                hasCorrectResultsRegardlessOfPushdown();
             }
             return this;
         }
 
-        private void verifyResultsWithPushdownDisabled()
+        @CanIgnoreReturnValue
+        public QueryAssert hasCorrectResultsRegardlessOfPushdown()
         {
             Session withoutPushdown = Session.builder(session)
                     .setSystemProperty("allow_pushdown_into_connectors", "false")
                     .build();
             matches(runner.execute(withoutPushdown, query));
+            return this;
         }
     }
 
diff --git a/plugin/trino-kudu/src/test/java/io/trino/plugin/kudu/TestKuduConnectorTest.java b/plugin/trino-kudu/src/test/java/io/trino/plugin/kudu/TestKuduConnectorTest.java
index a92fad6a8b5e..2d73b6e46c4a 100644
--- a/plugin/trino-kudu/src/test/java/io/trino/plugin/kudu/TestKuduConnectorTest.java
+++ b/plugin/trino-kudu/src/test/java/io/trino/plugin/kudu/TestKuduConnectorTest.java
@@ -620,6 +620,15 @@ public void testDateYearOfEraPredicate()
                 .hasStackTraceContaining("Cannot apply operator: varchar = date");
     }
 
+    @Override
+    public void testVarcharCastToDateInPredicate()
+    {
+        assertThatThrownBy(super::testVarcharCastToDateInPredicate)
+                .hasStackTraceContaining("Table partitioning must be specified using setRangePartitionColumns or addHashPartitions");
+
+        throw new SkipException("TODO: implement the test for Kudu");
+    }
+
     @Test
     @Override
     public void testCharVarcharComparison()
diff --git a/testing/trino-testing/src/main/java/io/trino/testing/BaseConnectorTest.java b/testing/trino-testing/src/main/java/io/trino/testing/BaseConnectorTest.java
index 3bb01b32cfd1..a21dad966315 100644
--- a/testing/trino-testing/src/main/java/io/trino/testing/BaseConnectorTest.java
+++ b/testing/trino-testing/src/main/java/io/trino/testing/BaseConnectorTest.java
@@ -503,6 +503,49 @@ public void testSortItemsReflectedInExplain()
                 expectedPattern);
     }
 
+    // CAST(a_varchar AS date) = DATE '...' is an interesting condition which may want to be optimized by the engine or a connector
+    @Test
+    public void testVarcharCastToDateInPredicate()
+    {
+        skipTestUnless(hasBehavior(SUPPORTS_CREATE_TABLE_WITH_DATA));
+
+        try (TestTable table = new TestTable(
+                getQueryRunner()::execute,
+                "varchar_as_date_pred",
+                "(a varchar)",
+                List.of(
+                        "'999-09-09'",
+                        "'1005-09-09'",
+                        "'2005-06-06'", "'2005-06-6'", "'2005-6-06'", "'2005-6-6'", "' 2005-06-06'", "'2005-06-06 '", "' +2005-06-06'", "'02005-06-06'",
+                        "'2005-09-06'", "'2005-09-6'", "'2005-9-06'", "'2005-9-6'", "' 2005-09-06'", "'2005-09-06 '", "' +2005-09-06'", "'02005-09-06'",
+                        "'2005-09-09'", "'2005-09-9'", "'2005-9-09'", "'2005-9-9'", "' 2005-09-09'", "'2005-09-09 '", "' +2005-09-09'", "'02005-09-09'",
+                        "'2005-09-10'", "'2005-9-10'", "' 2005-09-10'", "'2005-09-10 '", "' +2005-09-10'", "'02005-09-10'",
+                        "'9999-09-09'",
+                        "'99999-09-09'"))) {
+            for (String date : List.of("2005-09-06", "2005-09-09", "2005-09-10")) {
+                for (String operator : List.of("=", "<=", "<", ">", ">=", "!=", "IS DISTINCT FROM", "IS NOT DISTINCT FROM")) {
+                    assertThat(query("SELECT a FROM %s WHERE CAST(a AS date) %s DATE '%s'".formatted(table.getName(), operator, date)))
+                            .hasCorrectResultsRegardlessOfPushdown();
+                }
+            }
+        }
+
+        try (TestTable table = new TestTable(
+                getQueryRunner()::execute,
+                "varchar_as_date_pred",
+                "(a varchar)",
+                List.of("'2005-06-bad-date'", "'2005-09-10'"))) {
+            assertThatThrownBy(() -> query("SELECT a FROM %s WHERE CAST(a AS date) < DATE '2005-09-10'".formatted(table.getName())))
+                    .hasMessage("Value cannot be cast to date: 2005-06-bad-date");
+            // This failure isn't guaranteed. TODO make test more flexible when need arises.
+            assertThatThrownBy(() -> query("SELECT a FROM %s WHERE CAST(a AS date) = DATE '2005-09-10'".formatted(table.getName())))
+                    .hasMessage("Value cannot be cast to date: 2005-06-bad-date");
+            // This failure isn't guaranteed. TODO make test more flexible when need arises.
+            assertThatThrownBy(() -> query("SELECT a FROM %s WHERE CAST(a AS date) > DATE '2022-08-10'".formatted(table.getName())))
+                    .hasMessage("Value cannot be cast to date: 2005-06-bad-date");
+        }
+    }
+
     @Test
     public void testConcurrentScans()
     {