diff --git a/pkg/expression/builtin_compare.go b/pkg/expression/builtin_compare.go
index f837971e3901f..8e5c36707ec8f 100644
--- a/pkg/expression/builtin_compare.go
+++ b/pkg/expression/builtin_compare.go
@@ -1428,7 +1428,10 @@ func RefineComparedConstant(ctx BuildContext, targetFieldType types.FieldType, c
 		targetFieldType = *types.NewFieldType(mysql.TypeLonglong)
 	}
 	var intDatum types.Datum
-	intDatum, err = dt.ConvertTo(evalCtx.TypeCtx(), &targetFieldType)
+	// Disable AllowNegativeToUnsigned to make sure return 0 when underflow happens.
+	oriTypeCtx := evalCtx.TypeCtx()
+	newTypeCtx := oriTypeCtx.WithFlags(oriTypeCtx.Flags().WithAllowNegativeToUnsigned(false))
+	intDatum, err = dt.ConvertTo(newTypeCtx, &targetFieldType)
 	if err != nil {
 		if terror.ErrorEqual(err, types.ErrOverflow) {
 			return &Constant{
diff --git a/tests/integrationtest/r/expression/cast.result b/tests/integrationtest/r/expression/cast.result
index d54c9aea37ea1..76c9977dc52fb 100644
--- a/tests/integrationtest/r/expression/cast.result
+++ b/tests/integrationtest/r/expression/cast.result
@@ -118,3 +118,33 @@ select null as a union all select 'a' as a;
 a
 NULL
 a
+drop table if exists t0;
+create table t0(c0 tinyint(1) unsigned not null );
+insert into t0 values (1);
+select * from t0 where case 0 when t0.c0 > -1.194192591e9 then null else 1 end;
+c0
+1
+select t0.c0 > -1.194192591e9 from t0;
+t0.c0 > -1.194192591e9
+1
+select t0.c0 < -1.194192591e9 from t0;
+t0.c0 < -1.194192591e9
+0
+select -1.194192591e9 > t0.c0 from t0;
+-1.194192591e9 > t0.c0
+0
+select -1.194192591e9 < t0.c0 from t0;
+-1.194192591e9 < t0.c0
+1
+select t0.c0 > 1.194192591e9 from t0;
+t0.c0 > 1.194192591e9
+0
+select t0.c0 < 1.194192591e9 from t0;
+t0.c0 < 1.194192591e9
+1
+select 1.194192591e9 > t0.c0 from t0;
+1.194192591e9 > t0.c0
+1
+select 1.194192591e9 < t0.c0 from t0;
+1.194192591e9 < t0.c0
+0
diff --git a/tests/integrationtest/t/expression/cast.test b/tests/integrationtest/t/expression/cast.test
index 854daad9756b5..03843628ab9e6 100644
--- a/tests/integrationtest/t/expression/cast.test
+++ b/tests/integrationtest/t/expression/cast.test
@@ -73,3 +73,17 @@ select cast(cast('14:15' as time) as year) = YEAR(CURDATE());
 explain select null as a union all select 'a' as a;
 --sorted_result
 select null as a union all select 'a' as a;
+
+# TestNegFloatConvertToUnsigned
+drop table if exists t0;
+create table t0(c0 tinyint(1) unsigned not null );
+insert into t0 values (1);
+select * from t0 where case 0 when t0.c0 > -1.194192591e9 then null else 1 end;
+select t0.c0 > -1.194192591e9 from t0;
+select t0.c0 < -1.194192591e9 from t0;
+select -1.194192591e9 > t0.c0 from t0;
+select -1.194192591e9 < t0.c0 from t0;
+select t0.c0 > 1.194192591e9 from t0;
+select t0.c0 < 1.194192591e9 from t0;
+select 1.194192591e9 > t0.c0 from t0;
+select 1.194192591e9 < t0.c0 from t0;