diff --git a/executor/executor_test.go b/executor/executor_test.go
index f5b82c73c98aa..e932958d206d2 100644
--- a/executor/executor_test.go
+++ b/executor/executor_test.go
@@ -6647,3 +6647,19 @@ func (s *testSuite) TestIssue22201(c *C) {
 	tk.MustQuery("SELECT HEX(WEIGHT_STRING('ab' AS char(1000000000000000000)));").Check(testkit.Rows("<nil>"))
 	tk.MustQuery("show warnings").Check(testkit.Rows("Warning 1301 Result of weight_string() was larger than max_allowed_packet (67108864) - truncated"))
 }
+
+func (s *testSuite) TestIssue22231(c *C) {
+	tk := testkit.NewTestKit(c, s.store)
+	tk.MustExec("use test")
+	tk.MustExec("drop table if exists t_issue_22231")
+	tk.MustExec("create table t_issue_22231(a datetime)")
+	tk.MustExec("insert into t_issue_22231 values('2020--05-20 01:22:12')")
+	tk.MustQuery("select * from t_issue_22231 where a >= '2020-05-13 00:00:00 00:00:00' and a <= '2020-05-28 23:59:59 00:00:00'").Check(testkit.Rows("2020-05-20 01:22:12"))
+	tk.MustQuery("show warnings").Check(testkit.Rows("Warning 1292 Truncated incorrect datetime value: '2020-05-13 00:00:00 00:00:00'", "Warning 1292 Truncated incorrect datetime value: '2020-05-28 23:59:59 00:00:00'"))
+
+	tk.MustQuery("select cast('2020-10-22 10:31-10:12' as datetime)").Check(testkit.Rows("2020-10-22 10:31:10"))
+	tk.MustQuery("show warnings").Check(testkit.Rows("Warning 1292 Truncated incorrect datetime value: '2020-10-22 10:31-10:12'"))
+	tk.MustQuery("select cast('2020-05-28 23:59:59 00:00:00' as datetime)").Check(testkit.Rows("2020-05-28 23:59:59"))
+	tk.MustQuery("show warnings").Check(testkit.Rows("Warning 1292 Truncated incorrect datetime value: '2020-05-28 23:59:59 00:00:00'"))
+	tk.MustExec("drop table if exists t_issue_22231")
+}
diff --git a/types/time.go b/types/time.go
index 842c62daaf5f8..4a88001eda1e2 100644
--- a/types/time.go
+++ b/types/time.go
@@ -739,8 +739,8 @@ func ParseDateFormat(format string) []string {
 		return nil
 	}
 
-	// Date format must start and end with number.
-	if !isDigit(format[0]) || !isDigit(format[len(format)-1]) {
+	// Date format must start with number.
+	if !isDigit(format[0]) {
 		return nil
 	}
 
@@ -786,7 +786,14 @@ func isValidSeparator(c byte, prevParts int) bool {
 		return true
 	}
 
-	return prevParts == 2 && (c == ' ' || c == 'T')
+	if prevParts == 2 && (c == ' ' || c == 'T') {
+		return true
+	}
+
+	if prevParts > 4 && !isDigit(c) {
+		return true
+	}
+	return false
 }
 
 var validIdxCombinations = map[int]struct {
@@ -995,6 +1002,8 @@ func parseDatetime(sc *stmtctx.StatementContext, str string, fsp int8, isFloat b
 		}
 	}
 	switch len(seps) {
+	case 0:
+		return ZeroDatetime, errors.Trace(ErrWrongValue.GenWithStackByArgs(DateTimeStr, str))
 	case 1:
 		l := len(seps[0])
 		// Values specified as numbers
@@ -1083,6 +1092,8 @@ func parseDatetime(sc *stmtctx.StatementContext, str string, fsp int8, isFloat b
 			sc.AppendWarning(ErrTruncatedWrongVal.GenWithStackByArgs("datetime", str))
 			err = nil
 		}
+	case 2:
+		return ZeroDatetime, errors.Trace(ErrWrongValue.GenWithStackByArgs(DateTimeStr, str))
 	case 3:
 		// YYYY-MM-DD
 		err = scanTimeArgs(seps, &year, &month, &day)
@@ -1098,7 +1109,14 @@ func parseDatetime(sc *stmtctx.StatementContext, str string, fsp int8, isFloat b
 		err = scanTimeArgs(seps, &year, &month, &day, &hour, &minute, &second)
 		hhmmss = true
 	default:
-		return ZeroDatetime, errors.Trace(ErrWrongValue.GenWithStackByArgs(DateTimeStr, str))
+		// For case like `2020-05-28 23:59:59 00:00:00`, the seps should be > 6, the reluctant parts should be truncated.
+		seps = seps[:6]
+		// YYYY-MM-DD HH-MM-SS
+		if sc != nil {
+			sc.AppendWarning(ErrTruncatedWrongVal.GenWithStackByArgs("datetime", str))
+		}
+		err = scanTimeArgs(seps, &year, &month, &day, &hour, &minute, &second)
+		hhmmss = true
 	}
 	if err != nil {
 		return ZeroDatetime, errors.Trace(err)
diff --git a/types/time_test.go b/types/time_test.go
index 0befea3a77f1b..9dc3c4851e486 100644
--- a/types/time_test.go
+++ b/types/time_test.go
@@ -106,6 +106,15 @@ func (s *testTimeSuite) TestDateTime(c *C) {
 		{"2018.01.01 00:00:00", "2018-01-01 00:00:00"},
 		{"2018/01/01-00:00:00", "2018-01-01 00:00:00"},
 		{"4710072", "2047-10-07 02:00:00"},
+		{"2016-06-01 00:00:00 00:00:00", "2016-06-01 00:00:00"},
+		{"2020-06-01 00:00:00ads!,?*da;dsx", "2020-06-01 00:00:00"},
+
+		// For issue 22231
+		{"2020-05-28 23:59:59 00:00:00", "2020-05-28 23:59:59"},
+		{"2020-05-28 23:59:59-00:00:00", "2020-05-28 23:59:59"},
+		{"2020-05-28 23:59:59T T00:00:00", "2020-05-28 23:59:59"},
+		{"2020-10-22 10:31-10:12", "2020-10-22 10:31:10"},
+		{"2018.01.01 01:00:00", "2018-01-01 01:00:00"},
 	}
 
 	for _, test := range table {
@@ -164,12 +173,12 @@ func (s *testTimeSuite) TestDateTime(c *C) {
 		"170118-12",
 		"1710-10",
 		"1710-1000",
-		"2020-10-22 10:31-10:12", // YYYY-MM-DD HH:MM-SS:HH (invalid)
 	}
 
 	for _, test := range errTable {
 		_, err := types.ParseDatetime(sc, test)
-		c.Assert(err, NotNil)
+		c.Assert(err != nil || sc.WarningCount() > 0, Equals, true)
+		sc.SetWarnings(nil)
 	}
 }
 
@@ -1066,7 +1075,7 @@ func (s *testTimeSuite) TestParseDateFormat(c *C) {
 		{"2011-11-11  10:10:10", []string{"2011", "11", "11", "10", "10", "10"}},
 		{"xx2011-11-11 10:10:10", nil},
 		{"T10:10:10", nil},
-		{"2011-11-11x", nil},
+		{"2011-11-11x", []string{"2011", "11", "11x"}},
 		{"xxx 10:10:10", nil},
 	}