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/runner/setup/remote.sh b/test/runner/setup/remote.sh
index a23c164be0b..bb15c8d354a 100644
--- a/test/runner/setup/remote.sh
+++ b/test/runner/setup/remote.sh
@@ -43,7 +43,7 @@ elif [ "${platform}" = "rhel" ]; then
 fi
 
 if [ "${platform}" = "freebsd" ] || [ "${platform}" = "osx" ]; then
-    pip install virtualenv
+    pip install 'virtualenv<20'
 
     # Tests assume loopback addresses other than 127.0.0.1 will work.
     # Add aliases for loopback addresses used by tests.