diff --git a/tests/apiv2/test_milestones.py b/tests/apiv2/test_milestones.py
index db91c5ca9..7bcae053d 100644
--- a/tests/apiv2/test_milestones.py
+++ b/tests/apiv2/test_milestones.py
@@ -1,3 +1,4 @@
+from tests import randgen
 from tests.util import APITestCase
 from tracker import models
 from tracker.api import messages
@@ -18,13 +19,19 @@ def _format_milestone(self, milestone, with_event=True):
             'short_description': milestone.short_description,
             'start': milestone.start,
             'name': milestone.name,
+            'run': milestone.run_id,
             'visible': milestone.visible,
         }
 
     def setUp(self):
         super().setUp()
+        self.run = randgen.generate_runs(self.rand, self.event, 1, ordered=True)[0]
         self.public_milestone = models.Milestone.objects.create(
-            event=self.event, name='Public Milestone', amount=500.0, visible=True
+            event=self.event,
+            name='Public Milestone',
+            amount=500.0,
+            visible=True,
+            run=self.run,
         )
         self.hidden_milestone = models.Milestone.objects.create(
             event=self.event, name='Hidden Milestone', amount=1500.0, visible=False
@@ -43,7 +50,7 @@ def test_serializer(self):
         )
 
     def test_fetch(self):
-        with self.subTest('happy path'), self.saveSnapshot():
+        with self.saveSnapshot():
             with self.subTest('public'):
                 serialized = MilestoneSerializer(self.public_milestone)
                 data = self.get_detail(self.public_milestone)
@@ -83,6 +90,7 @@ def test_create(self):
                 data={
                     'name': 'New Milestone 2',
                     'amount': 1250,
+                    'run': self.run.pk,
                 },
                 user=self.add_user,
                 kwargs={'event_pk': self.event.pk},
@@ -134,6 +142,15 @@ def test_create(self):
                 },
                 status_code=403,
             )
+            self.post_new(
+                data={
+                    'name': 'Mismatched Event Milestone',
+                    'amount': 100,
+                    'event': self.blank_event.pk,
+                    'run': self.run.pk,
+                },
+                status_code=400,
+            )
             self.post_new(user=None, status_code=403)
 
         with self.subTest('user with locked permission'):
diff --git a/tests/test_api.py b/tests/test_api.py
index 27e7ab40a..aece95e0d 100755
--- a/tests/test_api.py
+++ b/tests/test_api.py
@@ -843,6 +843,7 @@ def format_milestone(cls, milestone, request):
                 description=milestone.description,
                 short_description=milestone.short_description,
                 public=str(milestone),
+                run=milestone.run_id,
                 visible=milestone.visible,
             ),
             model='tracker.milestone',
diff --git a/tests/util.py b/tests/util.py
index 10a3bc950..df12b5057 100644
--- a/tests/util.py
+++ b/tests/util.py
@@ -549,19 +549,19 @@ def _compare_value(self, key, expected, found):
     def _compare_model(
         self, expected_model, found_model, partial, prefix='', *, missing_ok=None
     ):
-        missing_ok = missing_ok or []
+        missing_ok = set(missing_ok or [])
         self.assertIsInstance(found_model, dict, 'found_model was not a dict')
         self.assertIsInstance(expected_model, dict, 'expected_model was not a dict')
+        found_keys = set(found_model.keys())
+        expected_keys = set(expected_model.keys())
         if partial:
             extra_keys = []
         else:
-            extra_keys = set(found_model.keys()) - set(expected_model.keys())
-        missing_keys = (
-            set(expected_model.keys()) - set(found_model.keys()) - set(missing_ok)
-        )
+            extra_keys = found_keys - expected_keys
+        missing_keys = expected_keys - found_keys - missing_ok
         unequal_keys = [
             k
-            for k in expected_model.keys()
+            for k in expected_keys
             if k in found_model
             and not isinstance(found_model[k], (list, dict))
             and not self._compare_value(k, expected_model[k], found_model[k])
@@ -574,10 +574,11 @@ def _compare_model(
                     found_model[k],
                     partial,
                     prefix=k,
-                    missing_ok=missing_ok,
+                    missing_ok=missing_ok
+                    | {'event'},  # always ok to be missing 'event' on nested objects
                 ),
             )
-            for k in expected_model.keys()
+            for k in expected_keys
             if k in found_model and isinstance(found_model[k], dict)
         ]
         nested_objects = [n for n in nested_objects if n[1]]
@@ -585,7 +586,7 @@ def _compare_model(
             f'{prefix}.' if prefix else '' + f'{k}': self._compare_lists(
                 expected_model[k], found_model[k], partial, prefix=k
             )
-            for k in expected_model.keys()
+            for k in expected_keys
             if k in found_model and isinstance(found_model[k], list)
         }
         for k, v in nested_list_keys.items():
diff --git a/tracker/admin/donation.py b/tracker/admin/donation.py
index 675c7ca9d..b059d5114 100644
--- a/tracker/admin/donation.py
+++ b/tracker/admin/donation.py
@@ -401,7 +401,7 @@ def merge_donors(self, request, queryset):
 
 @register(models.Milestone)
 class MilestoneAdmin(EventLockedMixin, EventReadOnlyMixin, CustomModelAdmin):
-    autocomplete_fields = ('event',)
+    autocomplete_fields = ('event', 'run')
     search_fields = ('name', 'description', 'short_description')
     list_filter = ('event',)
     list_display = ('name', 'event', 'start', 'amount', 'visible')
diff --git a/tracker/api/serializers.py b/tracker/api/serializers.py
index fee6024ea..6858cd8c5 100644
--- a/tracker/api/serializers.py
+++ b/tracker/api/serializers.py
@@ -12,6 +12,7 @@
 from django.utils.translation import gettext_lazy as _
 from rest_framework import serializers
 from rest_framework.exceptions import ErrorDetail, ValidationError
+from rest_framework.relations import PrimaryKeyRelatedField
 from rest_framework.serializers import ListSerializer, as_serializer_error
 from rest_framework.utils import model_meta
 from rest_framework.validators import UniqueTogetherValidator
@@ -946,6 +947,7 @@ class MilestoneSerializer(
 ):
     type = ClassNameField()
     event = EventSerializer()
+    run = PrimaryKeyRelatedField(queryset=SpeedRun.objects.all(), required=False)
 
     class Meta:
         model = Milestone
@@ -956,6 +958,7 @@ class Meta:
             'start',
             'amount',
             'name',
+            'run',
             'visible',
             'description',
             'short_description',
diff --git a/tracker/migrations/0049_add_milestone_run.py b/tracker/migrations/0049_add_milestone_run.py
new file mode 100644
index 000000000..4c300681f
--- /dev/null
+++ b/tracker/migrations/0049_add_milestone_run.py
@@ -0,0 +1,19 @@
+# Generated by Django 5.1.4 on 2025-01-09 14:38
+
+import django.db.models.deletion
+from django.db import migrations, models
+
+
+class Migration(migrations.Migration):
+
+    dependencies = [
+        ('tracker', '0048_remove_old_ad_permission'),
+    ]
+
+    operations = [
+        migrations.AddField(
+            model_name='milestone',
+            name='run',
+            field=models.ForeignKey(blank=True, default=None, null=True, on_delete=django.db.models.deletion.SET_NULL, to='tracker.speedrun'),
+        ),
+    ]
diff --git a/tracker/models/donation.py b/tracker/models/donation.py
index e5f4121d7..1f7bd2323 100644
--- a/tracker/models/donation.py
+++ b/tracker/models/donation.py
@@ -663,6 +663,13 @@ class Milestone(models.Model):
         validators=[positive, nonzero],
     )
     name = models.CharField(max_length=64)
+    run = models.ForeignKey(
+        'tracker.SpeedRun',
+        blank=True,
+        null=True,
+        default=None,
+        on_delete=models.SET_NULL,
+    )
     visible = models.BooleanField(default=False)
     description = models.TextField(max_length=1024, blank=True)
     short_description = models.TextField(
@@ -675,6 +682,8 @@ class Milestone(models.Model):
     def clean(self):
         if self.start >= self.amount:
             raise ValidationError({'start': 'start must be less than amount'})
+        if self.run_id and self.run.event_id != self.event_id:
+            raise ValidationError({'run': 'Run does not belong to that event'})
 
     def __str__(self):
         return f'{self.event.name} -- {self.name} -- {self.amount}'