diff --git a/CHANGELOG.md b/CHANGELOG.md
index e253c5737afa..cb7f45e49f29 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -6,6 +6,8 @@ IMPROVEMENTS:
 
 BUG FIXES:
  * core: *Fix restoration of stopped periodic jobs [GH-3201]
+ * core: Fix a race condition in which scheduling results from one invocation of
+   the scheduler wouldn't be considered by the next for the same job [GH-3206]
  * api: Sort /v1/agent/servers output so that output of Consul checks does not
    change [GH-3214]
  * api: Fix search handling of jobs with more than four hyphens and case were
diff --git a/nomad/eval_endpoint.go b/nomad/eval_endpoint.go
index 7b50c313a60a..9b5cd3cdce90 100644
--- a/nomad/eval_endpoint.go
+++ b/nomad/eval_endpoint.go
@@ -6,6 +6,7 @@ import (
 
 	"github.com/armon/go-metrics"
 	"github.com/hashicorp/go-memdb"
+	multierror "github.com/hashicorp/go-multierror"
 	"github.com/hashicorp/nomad/nomad/state"
 	"github.com/hashicorp/nomad/nomad/structs"
 	"github.com/hashicorp/nomad/scheduler"
@@ -92,8 +93,24 @@ func (e *Eval) Dequeue(args *structs.EvalDequeueRequest,
 
 	// Provide the output if any
 	if eval != nil {
+		// Get the index that the worker should wait until before scheduling.
+		waitIndex, err := e.getWaitIndex(eval.Namespace, eval.JobID)
+		if err != nil {
+			var mErr multierror.Error
+			multierror.Append(&mErr, err)
+
+			// We have dequeued the evaluation but won't be returning it to the
+			// worker so Nack the eval.
+			if err := e.srv.evalBroker.Nack(eval.ID, token); err != nil {
+				multierror.Append(&mErr, err)
+			}
+
+			return &mErr
+		}
+
 		reply.Eval = eval
 		reply.Token = token
+		reply.WaitIndex = waitIndex
 	}
 
 	// Set the query response
@@ -101,6 +118,31 @@ func (e *Eval) Dequeue(args *structs.EvalDequeueRequest,
 	return nil
 }
 
+// getWaitIndex returns the wait index that should be used by the worker before
+// invoking the scheduler. The index should be the highest modify index of any
+// evaluation for the job. This prevents scheduling races for the same job when
+// there are blocked evaluations.
+func (e *Eval) getWaitIndex(namespace, job string) (uint64, error) {
+	snap, err := e.srv.State().Snapshot()
+	if err != nil {
+		return 0, err
+	}
+
+	evals, err := snap.EvalsByJob(nil, namespace, job)
+	if err != nil {
+		return 0, err
+	}
+
+	var max uint64
+	for _, eval := range evals {
+		if max < eval.ModifyIndex {
+			max = eval.ModifyIndex
+		}
+	}
+
+	return max, nil
+}
+
 // Ack is used to acknowledge completion of a dequeued evaluation
 func (e *Eval) Ack(args *structs.EvalAckRequest,
 	reply *structs.GenericResponse) error {
diff --git a/nomad/eval_endpoint_test.go b/nomad/eval_endpoint_test.go
index 3330eda43552..9cf1b21a1df6 100644
--- a/nomad/eval_endpoint_test.go
+++ b/nomad/eval_endpoint_test.go
@@ -170,6 +170,56 @@ func TestEvalEndpoint_Dequeue(t *testing.T) {
 	if token != resp.Token {
 		t.Fatalf("bad token: %#v %#v", token, resp.Token)
 	}
+
+	if resp.WaitIndex != eval1.ModifyIndex {
+		t.Fatalf("bad wait index; got %d; want %d", resp.WaitIndex, eval1.ModifyIndex)
+	}
+}
+
+func TestEvalEndpoint_Dequeue_WaitIndex(t *testing.T) {
+	t.Parallel()
+	s1 := testServer(t, func(c *Config) {
+		c.NumSchedulers = 0 // Prevent automatic dequeue
+	})
+	defer s1.Shutdown()
+	codec := rpcClient(t, s1)
+	testutil.WaitForLeader(t, s1.RPC)
+
+	// Create the register request
+	eval1 := mock.Eval()
+	eval2 := mock.Eval()
+	eval2.JobID = eval1.JobID
+	s1.fsm.State().UpsertEvals(1000, []*structs.Evaluation{eval1})
+	s1.evalBroker.Enqueue(eval1)
+	s1.fsm.State().UpsertEvals(1001, []*structs.Evaluation{eval2})
+
+	// Dequeue the eval
+	get := &structs.EvalDequeueRequest{
+		Schedulers:       defaultSched,
+		SchedulerVersion: scheduler.SchedulerVersion,
+		WriteRequest:     structs.WriteRequest{Region: "global"},
+	}
+	var resp structs.EvalDequeueResponse
+	if err := msgpackrpc.CallWithCodec(codec, "Eval.Dequeue", get, &resp); err != nil {
+		t.Fatalf("err: %v", err)
+	}
+
+	if !reflect.DeepEqual(eval1, resp.Eval) {
+		t.Fatalf("bad: %v %v", eval1, resp.Eval)
+	}
+
+	// Ensure outstanding
+	token, ok := s1.evalBroker.Outstanding(eval1.ID)
+	if !ok {
+		t.Fatalf("should be outstanding")
+	}
+	if token != resp.Token {
+		t.Fatalf("bad token: %#v %#v", token, resp.Token)
+	}
+
+	if resp.WaitIndex != 1001 {
+		t.Fatalf("bad wait index; got %d; want %d", resp.WaitIndex, 1001)
+	}
 }
 
 func TestEvalEndpoint_Dequeue_Version_Mismatch(t *testing.T) {
diff --git a/nomad/structs/structs.go b/nomad/structs/structs.go
index 832ee4764401..578d93dbac8e 100644
--- a/nomad/structs/structs.go
+++ b/nomad/structs/structs.go
@@ -932,9 +932,29 @@ type SingleEvalResponse struct {
 type EvalDequeueResponse struct {
 	Eval  *Evaluation
 	Token string
+
+	// WaitIndex is the Raft index the worker should wait until invoking the
+	// scheduler.
+	WaitIndex uint64
+
 	QueryMeta
 }
 
+// GetWaitIndex is used to retrieve the Raft index in which state should be at
+// or beyond before invoking the scheduler.
+func (e *EvalDequeueResponse) GetWaitIndex() uint64 {
+	// Prefer the wait index sent. This will be populated on all responses from
+	// 0.7.0 and above
+	if e.WaitIndex != 0 {
+		return e.WaitIndex
+	} else if e.Eval != nil {
+		return e.Eval.ModifyIndex
+	}
+
+	// This should never happen
+	return 1
+}
+
 // PlanResponse is used to return from a PlanRequest
 type PlanResponse struct {
 	Result *PlanResult
diff --git a/nomad/worker.go b/nomad/worker.go
index 0a6b66cc3288..76fb4eefacf6 100644
--- a/nomad/worker.go
+++ b/nomad/worker.go
@@ -106,7 +106,7 @@ func (w *Worker) checkPaused() {
 func (w *Worker) run() {
 	for {
 		// Dequeue a pending evaluation
-		eval, token, shutdown := w.dequeueEvaluation(dequeueTimeout)
+		eval, token, waitIndex, shutdown := w.dequeueEvaluation(dequeueTimeout)
 		if shutdown {
 			return
 		}
@@ -118,7 +118,7 @@ func (w *Worker) run() {
 		}
 
 		// Wait for the raft log to catchup to the evaluation
-		if err := w.waitForIndex(eval.ModifyIndex, raftSyncLimit); err != nil {
+		if err := w.waitForIndex(waitIndex, raftSyncLimit); err != nil {
 			w.sendAck(eval.ID, token, false)
 			continue
 		}
@@ -136,7 +136,8 @@ func (w *Worker) run() {
 
 // dequeueEvaluation is used to fetch the next ready evaluation.
 // This blocks until an evaluation is available or a timeout is reached.
-func (w *Worker) dequeueEvaluation(timeout time.Duration) (*structs.Evaluation, string, bool) {
+func (w *Worker) dequeueEvaluation(timeout time.Duration) (
+	eval *structs.Evaluation, token string, waitIndex uint64, shutdown bool) {
 	// Setup the request
 	req := structs.EvalDequeueRequest{
 		Schedulers:       w.srv.config.EnabledSchedulers,
@@ -170,7 +171,7 @@ REQ:
 		}
 
 		if w.backoffErr(base, limit) {
-			return nil, "", true
+			return nil, "", 0, true
 		}
 		goto REQ
 	}
@@ -179,12 +180,12 @@ REQ:
 	// Check if we got a response
 	if resp.Eval != nil {
 		w.logger.Printf("[DEBUG] worker: dequeued evaluation %s", resp.Eval.ID)
-		return resp.Eval, resp.Token, false
+		return resp.Eval, resp.Token, resp.GetWaitIndex(), false
 	}
 
 	// Check for potential shutdown
 	if w.srv.IsShutdown() {
-		return nil, "", true
+		return nil, "", 0, true
 	}
 	goto REQ
 }
diff --git a/nomad/worker_test.go b/nomad/worker_test.go
index 3e716f31dc09..567a31321530 100644
--- a/nomad/worker_test.go
+++ b/nomad/worker_test.go
@@ -60,13 +60,16 @@ func TestWorker_dequeueEvaluation(t *testing.T) {
 	w := &Worker{srv: s1, logger: s1.logger}
 
 	// Attempt dequeue
-	eval, token, shutdown := w.dequeueEvaluation(10 * time.Millisecond)
+	eval, token, waitIndex, shutdown := w.dequeueEvaluation(10 * time.Millisecond)
 	if shutdown {
 		t.Fatalf("should not shutdown")
 	}
 	if token == "" {
 		t.Fatalf("should get token")
 	}
+	if waitIndex != eval1.ModifyIndex {
+		t.Fatalf("bad wait index; got %d; want %d", eval1.ModifyIndex)
+	}
 
 	// Ensure we get a sane eval
 	if !reflect.DeepEqual(eval, eval1) {
@@ -74,6 +77,76 @@ func TestWorker_dequeueEvaluation(t *testing.T) {
 	}
 }
 
+// Test that the worker picks up the correct wait index when there are multiple
+// evals for the same job.
+func TestWorker_dequeueEvaluation_SerialJobs(t *testing.T) {
+	t.Parallel()
+	s1 := testServer(t, func(c *Config) {
+		c.NumSchedulers = 0
+		c.EnabledSchedulers = []string{structs.JobTypeService}
+	})
+	defer s1.Shutdown()
+	testutil.WaitForLeader(t, s1.RPC)
+
+	// Create the evaluation
+	eval1 := mock.Eval()
+	eval2 := mock.Eval()
+	eval2.JobID = eval1.JobID
+
+	// Insert the evals into the state store
+	if err := s1.fsm.State().UpsertEvals(1000, []*structs.Evaluation{eval1, eval2}); err != nil {
+		t.Fatal(err)
+	}
+
+	s1.evalBroker.Enqueue(eval1)
+	s1.evalBroker.Enqueue(eval2)
+
+	// Create a worker
+	w := &Worker{srv: s1, logger: s1.logger}
+
+	// Attempt dequeue
+	eval, token, waitIndex, shutdown := w.dequeueEvaluation(10 * time.Millisecond)
+	if shutdown {
+		t.Fatalf("should not shutdown")
+	}
+	if token == "" {
+		t.Fatalf("should get token")
+	}
+	if waitIndex != eval1.ModifyIndex {
+		t.Fatalf("bad wait index; got %d; want %d", eval1.ModifyIndex)
+	}
+
+	// Ensure we get a sane eval
+	if !reflect.DeepEqual(eval, eval1) {
+		t.Fatalf("bad: %#v %#v", eval, eval1)
+	}
+
+	// Update the modify index of the first eval
+	if err := s1.fsm.State().UpsertEvals(2000, []*structs.Evaluation{eval1}); err != nil {
+		t.Fatal(err)
+	}
+
+	// Send the Ack
+	w.sendAck(eval1.ID, token, true)
+
+	// Attempt second dequeue
+	eval, token, waitIndex, shutdown = w.dequeueEvaluation(10 * time.Millisecond)
+	if shutdown {
+		t.Fatalf("should not shutdown")
+	}
+	if token == "" {
+		t.Fatalf("should get token")
+	}
+	if waitIndex != 2000 {
+		t.Fatalf("bad wait index; got %d; want 2000", eval2.ModifyIndex)
+	}
+
+	// Ensure we get a sane eval
+	if !reflect.DeepEqual(eval, eval2) {
+		t.Fatalf("bad: %#v %#v", eval, eval2)
+	}
+}
+
 func TestWorker_dequeueEvaluation_paused(t *testing.T) {
 	t.Parallel()
 	s1 := testServer(t, func(c *Config) {
@@ -101,7 +174,7 @@ func TestWorker_dequeueEvaluation_paused(t *testing.T) {
 
 	// Attempt dequeue
 	start := time.Now()
-	eval, token, shutdown := w.dequeueEvaluation(10 * time.Millisecond)
+	eval, token, waitIndex, shutdown := w.dequeueEvaluation(10 * time.Millisecond)
 	if diff := time.Since(start); diff < 100*time.Millisecond {
 		t.Fatalf("should have paused: %v", diff)
 	}
@@ -111,6 +184,9 @@ func TestWorker_dequeueEvaluation_paused(t *testing.T) {
 	if token == "" {
 		t.Fatalf("should get token")
 	}
+	if waitIndex != eval1.ModifyIndex {
+		t.Fatalf("bad wait index; got %d; want %d", eval1.ModifyIndex)
+	}
 
 	// Ensure we get a sane eval
 	if !reflect.DeepEqual(eval, eval1) {
@@ -136,7 +212,7 @@ func TestWorker_dequeueEvaluation_shutdown(t *testing.T) {
 	}()
 
 	// Attempt dequeue
-	eval, _, shutdown := w.dequeueEvaluation(10 * time.Millisecond)
+	eval, _, _, shutdown := w.dequeueEvaluation(10 * time.Millisecond)
 	if !shutdown {
 		t.Fatalf("should not shutdown")
 	}
@@ -164,7 +240,7 @@ func TestWorker_sendAck(t *testing.T) {
 	w := &Worker{srv: s1, logger: s1.logger}
 
 	// Attempt dequeue
-	eval, token, _ := w.dequeueEvaluation(10 * time.Millisecond)
+	eval, token, _, _ := w.dequeueEvaluation(10 * time.Millisecond)
 
 	// Check the depth is 0, 1 unacked
 	stats := s1.evalBroker.Stats()
@@ -182,7 +258,7 @@ func TestWorker_sendAck(t *testing.T) {
 	}
 
 	// Attempt dequeue
-	eval, token, _ = w.dequeueEvaluation(10 * time.Millisecond)
+	eval, token, _, _ = w.dequeueEvaluation(10 * time.Millisecond)
 
 	// Send the Ack
 	w.sendAck(eval.ID, token, true)