diff --git a/common/djangoapps/util/milestones_helpers.py b/common/djangoapps/util/milestones_helpers.py
index d1514d0dee..ad26ad238c 100644
--- a/common/djangoapps/util/milestones_helpers.py
+++ b/common/djangoapps/util/milestones_helpers.py
@@ -175,6 +175,18 @@ def fulfill_course_milestone(course_key, user):
         milestones_api.add_user_milestone({'id': user.id}, milestone)
 
 
+def remove_course_milestones(course_key, user, relationship):
+    """
+    Remove all user milestones for the course specified by course_key.
+    """
+    if not settings.FEATURES.get('MILESTONES_APP', False):
+        return None
+    from milestones import api as milestones_api
+    course_milestones = milestones_api.get_course_milestones(course_key=course_key, relationship=relationship)
+    for milestone in course_milestones:
+        milestones_api.remove_user_milestone({'id': user.id}, milestone)
+
+
 def get_required_content(course, user):
     """
     Queries milestones subsystem to see if the specified course is gated on one or more milestones,
@@ -321,6 +333,19 @@ def get_course_content_milestones(course_id, content_id, relationship):
     return milestones_api.get_course_content_milestones(course_id, content_id, relationship)
 
 
+def remove_course_content_user_milestones(course_key, content_key, user, relationship):
+    """
+    Removes the specified User-Milestone link from the system for the specified course content module.
+    """
+    if not settings.FEATURES.get('MILESTONES_APP', False):
+        return []
+    from milestones import api as milestones_api
+
+    course_content_milestones = milestones_api.get_course_content_milestones(course_key, content_key, relationship)
+    for milestone in course_content_milestones:
+        milestones_api.remove_user_milestone({'id': user.id}, milestone)
+
+
 def remove_content_references(content_id):
     """
     Client API operation adapter/wrapper
diff --git a/lms/djangoapps/instructor_task/api.py b/lms/djangoapps/instructor_task/api.py
index a1bb562536..5ad4cc07de 100644
--- a/lms/djangoapps/instructor_task/api.py
+++ b/lms/djangoapps/instructor_task/api.py
@@ -38,6 +38,7 @@ from instructor_task.api_helper import (
     submit_task,
 )
 from bulk_email.models import CourseEmail
+from util import milestones_helpers
 
 
 def get_running_instructor_tasks(course_id):
@@ -269,6 +270,8 @@ def submit_delete_entrance_exam_state_for_student(request, usage_key, student):
     Module state for all problems in entrance exam will be deleted
     for specified student.
 
+    All User Milestones of entrance exam will be removed for the specified student
+
     Parameters are `usage_key`, which must be a :class:`Location`
     representing entrance exam section and the `student` as a User object.
 
@@ -286,6 +289,14 @@ def submit_delete_entrance_exam_state_for_student(request, usage_key, student):
     # check arguments:  make sure entrance exam(section) exists for given usage_key
     modulestore().get_item(usage_key)
 
+    # Remove Content milestones that user has completed
+    milestones_helpers.remove_course_content_user_milestones(
+        course_key=usage_key.course_key,
+        content_key=usage_key,
+        user=student,
+        relationship='fulfills'
+    )
+
     task_type = 'delete_problem_state'
     task_class = delete_problem_state
     task_input, task_key = encode_entrance_exam_and_student_input(usage_key, student)