diff --git a/CHANGELOG.md b/CHANGELOG.md
index 3d6d9cc05..7e444dc09 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -4,7 +4,7 @@
 
 - Updated pip from 23.0.1 to 23.1.2. ([#1441](https://github.com/heroku/heroku-buildpack-python/pull/1441))
 - Updated setuptools from 67.6.1 to 67.7.2. ([#1441](https://github.com/heroku/heroku-buildpack-python/pull/1441))
-- The pip bootstrap step is now performed using the pip wheel bundled with the Python stdlib, rather than one downloaded from S3. ([#1442](https://github.com/heroku/heroku-buildpack-python/pull/1442))
+- The pip bootstrap step is now performed using the pip wheel bundled with the Python stdlib, rather than one downloaded from S3. ([#1442](https://github.com/heroku/heroku-buildpack-python/pull/1442) and [#1444](https://github.com/heroku/heroku-buildpack-python/pull/1444))
 
 ## v231 (2023-04-12)
 
diff --git a/bin/steps/python b/bin/steps/python
index 9ec44a3cf..e00b142da 100755
--- a/bin/steps/python
+++ b/bin/steps/python
@@ -182,8 +182,12 @@ puts-step "Installing pip ${PIP_VERSION}, setuptools ${SETUPTOOLS_VERSION} and w
 # Python bundles Pip within its standard library, which we can use to install our chosen
 # pip version from PyPI, saving us from having to download the usual pip bootstrap script.
 # We have to use a glob since the bundled wheel filename contains the pip version, which
-# differs between Python versions.
-BUNDLED_PIP_WHEEL="$(compgen -G ".heroku/python/lib/python*/ensurepip/_bundled/pip-*.whl" || true)"
+# differs between Python versions. We also have to handle the case where there are multiple
+# matching pip wheels, since in some versions of Python (eg 3.9.0) multiple versions of pip
+# were accidentally bundled upstream. Note: This implementation relies upon `nullglob` being
+# set, which is the case thanks to the `bin/utils` that was run earlier.
+BUNDLED_PIP_WHEEL_LIST=(.heroku/python/lib/python*/ensurepip/_bundled/pip-*.whl)
+BUNDLED_PIP_WHEEL="${BUNDLED_PIP_WHEEL_LIST[0]}"
 
 if [[ -z "${BUNDLED_PIP_WHEEL}" ]]; then
   mcount "failure.python.locate-bundled-pip-wheel"