diff --git a/syncer/checkpoint.go b/syncer/checkpoint.go
index 0514494f16..c1ec325f24 100644
--- a/syncer/checkpoint.go
+++ b/syncer/checkpoint.go
@@ -145,8 +145,8 @@ type CheckPoint interface {
 	// DeleteTablePoint deletes checkpoint for specified table in memory and storage
 	DeleteTablePoint(tctx *tcontext.Context, sourceSchema, sourceTable string) error
 
-	// IsNewerTablePoint checks whether job's checkpoint is newer than previous saved checkpoint
-	IsNewerTablePoint(sourceSchema, sourceTable string, pos mysql.Position) bool
+	// IsOlderThanTablePoint checks whether job's checkpoint is older than previous saved checkpoint
+	IsOlderThanTablePoint(sourceSchema, sourceTable string, pos mysql.Position, useLE bool) bool
 
 	// SaveGlobalPoint saves the global binlog stream's checkpoint
 	// corresponding to Meta.Save
@@ -327,20 +327,26 @@ func (cp *RemoteCheckPoint) DeleteTablePoint(tctx *tcontext.Context, sourceSchem
 	return nil
 }
 
-// IsNewerTablePoint implements CheckPoint.IsNewerTablePoint
-func (cp *RemoteCheckPoint) IsNewerTablePoint(sourceSchema, sourceTable string, pos mysql.Position) bool {
+// IsOlderThanTablePoint implements CheckPoint.IsOlderThanTablePoint.
+// For binlog position replication, currently DM will split rows changes of an event to jobs, so some job may has save position.
+// if useLE is true, we use less than or equal.
+func (cp *RemoteCheckPoint) IsOlderThanTablePoint(sourceSchema, sourceTable string, pos mysql.Position, useLE bool) bool {
 	cp.RLock()
 	defer cp.RUnlock()
 	mSchema, ok := cp.points[sourceSchema]
 	if !ok {
-		return true
+		return false
 	}
 	point, ok := mSchema[sourceTable]
 	if !ok {
-		return true
+		return false
 	}
 	oldPos := point.MySQLPos()
-	return pos.Compare(oldPos) > 0
+	cp.logCtx.L().Debug("compare table position whether is newer", zap.Stringer("position", pos), zap.Stringer("old position", oldPos))
+	if useLE {
+		return pos.Compare(oldPos) <= 0
+	}
+	return pos.Compare(oldPos) < 0
 }
 
 // SaveGlobalPoint implements CheckPoint.SaveGlobalPoint
diff --git a/syncer/checkpoint_test.go b/syncer/checkpoint_test.go
index 00a318309f..c6df4f1f4c 100644
--- a/syncer/checkpoint_test.go
+++ b/syncer/checkpoint_test.go
@@ -269,23 +269,23 @@ func (s *testCheckpointSuite) testTableCheckPoint(c *C, cp CheckPoint) {
 	)
 
 	// not exist
-	newer := cp.IsNewerTablePoint(schema, table, pos1)
-	c.Assert(newer, IsTrue)
+	older := cp.IsOlderThanTablePoint(schema, table, pos1, false)
+	c.Assert(older, IsFalse)
 
 	// save
 	cp.SaveTablePoint(schema, table, pos2)
-	newer = cp.IsNewerTablePoint(schema, table, pos1)
-	c.Assert(newer, IsFalse)
+	older = cp.IsOlderThanTablePoint(schema, table, pos1, false)
+	c.Assert(older, IsTrue)
 
 	// rollback, to min
 	cp.Rollback()
-	newer = cp.IsNewerTablePoint(schema, table, pos1)
-	c.Assert(newer, IsTrue)
+	older = cp.IsOlderThanTablePoint(schema, table, pos1, false)
+	c.Assert(older, IsFalse)
 
 	// save again
 	cp.SaveTablePoint(schema, table, pos2)
-	newer = cp.IsNewerTablePoint(schema, table, pos1)
-	c.Assert(newer, IsFalse)
+	older = cp.IsOlderThanTablePoint(schema, table, pos1, false)
+	c.Assert(older, IsTrue)
 
 	// flush + rollback
 	s.mock.ExpectBegin()
@@ -294,8 +294,8 @@ func (s *testCheckpointSuite) testTableCheckPoint(c *C, cp CheckPoint) {
 	err = cp.FlushPointsExcept(tctx, nil, nil, nil)
 	c.Assert(err, IsNil)
 	cp.Rollback()
-	newer = cp.IsNewerTablePoint(schema, table, pos1)
-	c.Assert(newer, IsFalse)
+	older = cp.IsOlderThanTablePoint(schema, table, pos1, false)
+	c.Assert(older, IsTrue)
 
 	// clear, to min
 	s.mock.ExpectBegin()
@@ -303,13 +303,13 @@ func (s *testCheckpointSuite) testTableCheckPoint(c *C, cp CheckPoint) {
 	s.mock.ExpectCommit()
 	err = cp.Clear(tctx)
 	c.Assert(err, IsNil)
-	newer = cp.IsNewerTablePoint(schema, table, pos1)
-	c.Assert(newer, IsTrue)
+	older = cp.IsOlderThanTablePoint(schema, table, pos1, false)
+	c.Assert(older, IsFalse)
 
 	// save
 	cp.SaveTablePoint(schema, table, pos2)
-	newer = cp.IsNewerTablePoint(schema, table, pos1)
-	c.Assert(newer, IsFalse)
+	older = cp.IsOlderThanTablePoint(schema, table, pos1, false)
+	c.Assert(older, IsTrue)
 
 	// test save table point less than global point
 	func() {
@@ -330,6 +330,6 @@ func (s *testCheckpointSuite) testTableCheckPoint(c *C, cp CheckPoint) {
 	err = cp.FlushPointsExcept(tctx, [][]string{{schema, table}}, nil, nil)
 	c.Assert(err, IsNil)
 	cp.Rollback()
-	newer = cp.IsNewerTablePoint(schema, table, pos1)
-	c.Assert(newer, IsTrue)
+	older = cp.IsOlderThanTablePoint(schema, table, pos1, false)
+	c.Assert(older, IsFalse)
 }
diff --git a/syncer/syncer.go b/syncer/syncer.go
index 34de9b2c75..124f8ad44e 100644
--- a/syncer/syncer.go
+++ b/syncer/syncer.go
@@ -15,6 +15,7 @@ package syncer
 
 import (
 	"context"
+	"errors"
 	"fmt"
 	"math"
 	"os"
@@ -751,7 +752,34 @@ func (s *Syncer) checkWait(job *job) bool {
 	return false
 }
 
+// only used in tests.
+var (
+	lastPos        mysql.Position
+	lastPosNum     int
+	waitJobsDone   bool
+	failExecuteSQL bool
+	failOnce       sync2.AtomicInt64
+)
+
 func (s *Syncer) addJob(job *job) error {
+	failpoint.Inject("countJobFromOneEvent", func() {
+		if job.currentPos.Compare(lastPos) == 0 {
+			lastPosNum++
+		} else {
+			lastPos = job.currentPos
+			lastPosNum = 1
+		}
+		// trigger a flush after see one job
+		if lastPosNum == 1 {
+			waitJobsDone = true
+			s.tctx.L().Info("meet the first job of an event", zap.Any("binlog position", lastPos))
+		}
+		// mock a execution error after see two jobs.
+		if lastPosNum == 2 {
+			failExecuteSQL = true
+			s.tctx.L().Info("meet the second job of an event", zap.Any("binlog position", lastPos))
+		}
+	})
 	var (
 		queueBucket int
 		execDDLReq  *pb.ExecDDLRequest
@@ -802,6 +830,13 @@ func (s *Syncer) addJob(job *job) error {
 	}
 
 	wait := s.checkWait(job)
+	failpoint.Inject("flushFirstJobOfEvent", func() {
+		if waitJobsDone {
+			s.tctx.L().Info("trigger flushFirstJobOfEvent")
+			waitJobsDone = false
+			wait = true
+		}
+	})
 	if wait {
 		s.jobWg.Wait()
 		s.c.reset()
@@ -1001,6 +1036,13 @@ func (s *Syncer) sync(tctx *tcontext.Context, queueBucket string, db *DBConn, jo
 		if len(jobs) == 0 {
 			return nil
 		}
+
+		failpoint.Inject("failSecondJobOfEvent", func() {
+			if failExecuteSQL && failOnce.CompareAndSwap(0, 1) {
+				s.tctx.L().Info("trigger failSecondJobOfEvent")
+				failpoint.Return(errors.New("failSecondJobOfEvent"))
+			}
+		})
 		queries := make([]string, 0, len(jobs))
 		args := make([][]interface{}, 0, len(jobs))
 		for _, j := range jobs {
@@ -1470,7 +1512,7 @@ func (s *Syncer) handleRowsEvent(ev *replication.RowsEvent, ec eventContext) err
 	}
 
 	// DML position before table checkpoint, ignore it
-	if !s.checkpoint.IsNewerTablePoint(originSchema, originTable, *ec.currentPos) {
+	if s.checkpoint.IsOlderThanTablePoint(originSchema, originTable, *ec.currentPos, false) {
 		s.tctx.L().Debug("ignore obsolete event that is old than table checkpoint", zap.String("event", "row"), log.WrapStringerField("position", ec.currentPos), zap.String("origin schema", originSchema), zap.String("origin table", originTable))
 		return nil
 	}
@@ -1700,7 +1742,7 @@ func (s *Syncer) handleQueryEvent(ev *replication.QueryEvent, ec eventContext) e
 
 		// for DDL, we wait it to be executed, so we can check if event is newer in this syncer's main process goroutine
 		// ignore obsolete DDL here can avoid to try-sync again for already synced DDLs
-		if !s.checkpoint.IsNewerTablePoint(tableNames[0][0].Schema, tableNames[0][0].Name, *ec.currentPos) {
+		if s.checkpoint.IsOlderThanTablePoint(tableNames[0][0].Schema, tableNames[0][0].Name, *ec.currentPos, true) {
 			s.tctx.L().Info("ignore obsolete DDL", zap.String("event", "query"), zap.String("statement", sql), log.WrapStringerField("position", ec.currentPos))
 			continue
 		}
diff --git a/tests/all_mode/data/db1.increment3.sql b/tests/all_mode/data/db1.increment3.sql
new file mode 100644
index 0000000000..87fc44acad
--- /dev/null
+++ b/tests/all_mode/data/db1.increment3.sql
@@ -0,0 +1,3 @@
+use all_mode;
+insert into t1 (id, name) values (10, '10'), (20, '20');
+insert into t1 (id, name) values (30, '30');
diff --git a/tests/all_mode/data/db2.increment3.sql b/tests/all_mode/data/db2.increment3.sql
new file mode 100644
index 0000000000..1d579a06d8
--- /dev/null
+++ b/tests/all_mode/data/db2.increment3.sql
@@ -0,0 +1,3 @@
+use all_mode;
+insert into t2 (id, name) values (10, '10'), (20, '20');
+insert into t2 (id, name) values (30, '30');
diff --git a/tests/all_mode/run.sh b/tests/all_mode/run.sh
index 8827314873..82d4133334 100755
--- a/tests/all_mode/run.sh
+++ b/tests/all_mode/run.sh
@@ -52,11 +52,54 @@ function test_session_config(){
     echo "[$(date)] <<<<<< finish test_session_config >>>>>>"
 }
 
-function run() {
+function test_fail_job_between_event() {
+	run_sql_file $cur/data/db1.prepare.sql $MYSQL_HOST1 $MYSQL_PORT1 $MYSQL_PASSWORD1
+	check_contains 'Query OK, 2 rows affected'
+	run_sql_file $cur/data/db2.prepare.sql $MYSQL_HOST2 $MYSQL_PORT2 $MYSQL_PASSWORD2
+	check_contains 'Query OK, 3 rows affected'
+
+	# start DM worker and master
+	run_dm_master $WORK_DIR/master $MASTER_PORT $cur/conf/dm-master.toml
+	check_rpc_alive $cur/../bin/check_master_online 127.0.0.1:$MASTER_PORT
+
+	inject_points=(
+		"github.com/pingcap/dm/dm/worker/TaskCheckInterval=return(\"500ms\")"
+		"github.com/pingcap/dm/syncer/countJobFromOneEvent=return()"
+		"github.com/pingcap/dm/syncer/flushFirstJobOfEvent=return()"
+		"github.com/pingcap/dm/syncer/failSecondJobOfEvent=return()"
+	)
+	export GO_FAILPOINTS="$(join_string \; ${inject_points[@]})"
+	run_dm_worker $WORK_DIR/worker1 $WORKER1_PORT $cur/conf/dm-worker1.toml
+	check_rpc_alive $cur/../bin/check_worker_online 127.0.0.1:$WORKER1_PORT
+	run_dm_worker $WORK_DIR/worker2 $WORKER2_PORT $cur/conf/dm-worker2.toml
+	check_rpc_alive $cur/../bin/check_worker_online 127.0.0.1:$WORKER2_PORT
+
+  cp $cur/conf/dm-task.yaml $WORK_DIR/dm-task.yaml
+	sed -i 's/sql_mode: ".*"/sql_mode: "NO_AUTO_VALUE_ON_ZERO"/g'  $WORK_DIR/dm-task.yaml
+  dmctl_start_task "$WORK_DIR/dm-task.yaml"
+
+	run_sql_file $cur/data/db1.increment3.sql $MYSQL_HOST1 $MYSQL_PORT1 $MYSQL_PASSWORD1
+	run_sql_file $cur/data/db2.increment3.sql $MYSQL_HOST2 $MYSQL_PORT2 $MYSQL_PASSWORD2
+	sleep 2
+	check_log_contains $WORK_DIR/worker1/log/dm-worker.log "failSecondJobOfEvent"
+	check_log_contains $WORK_DIR/worker2/log/dm-worker.log "failSecondJobOfEvent"
+	run_dm_ctl $WORK_DIR "127.0.0.1:$MASTER_PORT" \
+		"query-status test" \
+		"\"result\": true" 3
+	check_sync_diff $WORK_DIR $cur/conf/diff_config.toml
+
+	cleanup_data all_mode
+	cleanup_process $*
+
+	export GO_FAILPOINTS=''
+}
 
+function run() {
     run_sql "SET @@GLOBAL.SQL_MODE='ANSI_QUOTES,NO_AUTO_VALUE_ON_ZERO'" $MYSQL_PORT1 $MYSQL_PASSWORD1
     run_sql "SET @@GLOBAL.SQL_MODE='ANSI_QUOTES,NO_AUTO_VALUE_ON_ZERO'" $MYSQL_PORT2 $MYSQL_PASSWORD2
 
+    test_fail_job_between_event
+
     test_session_config
 
     export GO_FAILPOINTS="github.com/pingcap/dm/dm/worker/TaskCheckInterval=return(\"500ms\")"