diff --git a/changelogs/fragments/ansible-test-constraints-virtualenv.yml b/changelogs/fragments/ansible-test-constraints-virtualenv.yml
new file mode 100644
index 00000000000..5376448cb46
--- /dev/null
+++ b/changelogs/fragments/ansible-test-constraints-virtualenv.yml
@@ -0,0 +1,2 @@
+bugfixes:
+  - ansible-test - Use ``virtualenv`` versions before 20 on provisioned macOS instances to remain compatible with an older pip install.
diff --git a/test/lib/ansible_test/_data/setup/remote.sh b/test/lib/ansible_test/_data/setup/remote.sh
index 4cb8a233008..922bb2d5456 100644
--- a/test/lib/ansible_test/_data/setup/remote.sh
+++ b/test/lib/ansible_test/_data/setup/remote.sh
@@ -73,7 +73,7 @@ elif [ "${platform}" = "rhel" ]; then
 elif [ "${platform}" = "osx" ]; then
     while true; do
         pip install --disable-pip-version-check --quiet \
-            virtualenv \
+            'virtualenv<20' \
         && break
         echo "Failed to install packages. Sleeping before trying again..."
         sleep 10