diff --git a/fe/fe-core/src/main/java/org/apache/doris/nereids/trees/expressions/functions/executable/DateTimeExtractAndTransform.java b/fe/fe-core/src/main/java/org/apache/doris/nereids/trees/expressions/functions/executable/DateTimeExtractAndTransform.java
index 87e4b97379..8cda0c2d87 100644
--- a/fe/fe-core/src/main/java/org/apache/doris/nereids/trees/expressions/functions/executable/DateTimeExtractAndTransform.java
+++ b/fe/fe-core/src/main/java/org/apache/doris/nereids/trees/expressions/functions/executable/DateTimeExtractAndTransform.java
@@ -32,6 +32,7 @@ import org.apache.doris.nereids.trees.expressions.literal.SmallIntLiteral;
 import org.apache.doris.nereids.trees.expressions.literal.TinyIntLiteral;
 import org.apache.doris.nereids.trees.expressions.literal.VarcharLiteral;
 import org.apache.doris.nereids.types.DateTimeV2Type;
+import org.apache.doris.nereids.types.DateType;
 import org.apache.doris.nereids.types.DecimalV3Type;
 import org.apache.doris.nereids.types.VarcharType;
 import org.apache.doris.nereids.util.DateUtils;
@@ -593,8 +594,9 @@ public class DateTimeExtractAndTransform {
      */
     @ExecFunction(name = "makedate", argTypes = {"INT", "INT"}, returnType = "DATE")
     public static Expression makeDate(IntegerLiteral year, IntegerLiteral dayOfYear) {
-        return DateLiteral.fromJavaDateType(LocalDateTime.of(year.getValue(), 1, 1, 0, 0, 0)
-                .plusDays(dayOfYear.getValue() - 1));
+        int day = dayOfYear.getValue();
+        return day > 0 ? DateLiteral.fromJavaDateType(LocalDateTime.of(year.getValue(), 1, 1, 0, 0, 0)
+                .plusDays(day - 1)) : new NullLiteral(DateType.INSTANCE);
     }
 
     /**
diff --git a/fe/fe-core/src/main/java/org/apache/doris/nereids/util/DateUtils.java b/fe/fe-core/src/main/java/org/apache/doris/nereids/util/DateUtils.java
index 70f25b25fc..354d78d027 100644
--- a/fe/fe-core/src/main/java/org/apache/doris/nereids/util/DateUtils.java
+++ b/fe/fe-core/src/main/java/org/apache/doris/nereids/util/DateUtils.java
@@ -163,7 +163,7 @@ public class DateUtils {
                 getOrDefault(accessor, ChronoField.YEAR),
                 getOrDefault(accessor, ChronoField.MONTH_OF_YEAR),
                 getOrDefault(accessor, ChronoField.DAY_OF_MONTH),
-                getOrDefault(accessor, ChronoField.HOUR_OF_DAY),
+                getHourOrDefault(accessor),
                 getOrDefault(accessor, ChronoField.MINUTE_OF_HOUR),
                 getOrDefault(accessor, ChronoField.SECOND_OF_MINUTE),
                 getOrDefault(accessor, ChronoField.NANO_OF_SECOND));
@@ -173,6 +173,19 @@ public class DateUtils {
         return accessor.isSupported(field) ? accessor.get(field) : /* default value */ 0;
     }
 
+    /**
+     * get hour from accessor, if not support hour field, return 0
+     */
+    public static int getHourOrDefault(final TemporalAccessor accessor) {
+        if (accessor.isSupported(ChronoField.HOUR_OF_DAY)) {
+            return accessor.get(ChronoField.HOUR_OF_DAY);
+        } else if (accessor.isSupported(ChronoField.HOUR_OF_AMPM)) {
+            return accessor.get(ChronoField.HOUR_OF_AMPM);
+        } else {
+            return 0;
+        }
+    }
+
     public static ZoneId getTimeZone() {
         if (ConnectContext.get() == null || ConnectContext.get().getSessionVariable() == null) {
             return ZoneId.systemDefault();
diff --git a/regression-test/data/query_p0/sql_functions/datetime_functions/test_date_function.out b/regression-test/data/query_p0/sql_functions/datetime_functions/test_date_function.out
index 6a59c3c994..ecf83359db 100644
--- a/regression-test/data/query_p0/sql_functions/datetime_functions/test_date_function.out
+++ b/regression-test/data/query_p0/sql_functions/datetime_functions/test_date_function.out
@@ -234,7 +234,7 @@ Saturday
 0
 
 -- !sql --
-2021-01-01	2021-04-10	2022-02-04
+\N	2021-01-01	2021-04-10	2022-02-04
 
 -- !sql --
 59
@@ -272,6 +272,9 @@ February
 -- !sql --
 2014-12-21T12:34:56
 
+-- !sql --
+2011-11-09 11:09:30
+
 -- !sql --
 2014-12-21T12:34:56.789
 
diff --git a/regression-test/suites/query_p0/sql_functions/datetime_functions/test_date_function.groovy b/regression-test/suites/query_p0/sql_functions/datetime_functions/test_date_function.groovy
index f174819979..74163e2c53 100644
--- a/regression-test/suites/query_p0/sql_functions/datetime_functions/test_date_function.groovy
+++ b/regression-test/suites/query_p0/sql_functions/datetime_functions/test_date_function.groovy
@@ -299,7 +299,7 @@ suite("test_date_function") {
     qt_sql """ select hour('2018-12-31') """
 
     // MAKEDATE
-    qt_sql """ select makedate(2021,1), makedate(2021,100), makedate(2021,400) """
+    qt_sql """ select makedate(2021,0), makedate(2021,1), makedate(2021,100), makedate(2021,400) """
 
     // MINUTE
     qt_sql """ select minute('2018-12-31 23:59:59') """
@@ -332,6 +332,7 @@ suite("test_date_function") {
     qt_sql """ select str_to_date(test_datetime, '%Y-%m-%d %H:%i:%s') from ${tableName}; """
     qt_sql """ select str_to_date("", "%Y-%m-%d %H:%i:%s"); """
     qt_sql """ select str_to_date("2014-12-21 12:34%3A56", '%Y-%m-%d %H:%i%%3A%s'); """
+    qt_sql """ select str_to_date('11.09.2011 11:09:30', '%m.%d.%Y %h:%i:%s'); """
     qt_sql """ select str_to_date("2014-12-21 12:34:56.789 PM", '%Y-%m-%d %h:%i:%s.%f %p'); """
     qt_sql """ select str_to_date('2023-07-05T02:09:55.880Z','%Y-%m-%dT%H:%i:%s.%fZ') """
     qt_sql """ select str_to_date('200442 Monday', '%X%V %W') """