diff --git a/manifests/p/Python/Python/2/2.7.16/Python.Python.2.installer.yaml b/manifests/p/Python/Python/2/2.7.16/Python.Python.2.installer.yaml
new file mode 100644
index 000000000..674bdbdd3
--- /dev/null
+++ b/manifests/p/Python/Python/2/2.7.16/Python.Python.2.installer.yaml
@@ -0,0 +1,19 @@
+# yaml-language-server: $schema=https://aka.ms/winget-manifest.installer.1.0.0.schema.json
+PackageIdentifier: Python.Python.2
+PackageVersion: 2.7.16
+FileExtensions:
+- py
+- pyw
+- pyc
+- pyo
+InstallerType: msi
+Installers:
+- Architecture: x64
+  InstallerUrl: https://www.python.org/ftp/python/2.7.16/python-2.7.16.amd64.msi
+  InstallerSha256: 7C0F45993019152D46041A7DB4B947B919558FDB7A8F67BCD0535BC98D42B603
+- Architecture: x86
+  InstallerUrl: https://www.python.org/ftp/python/2.7.16/python-2.7.16.msi
+  InstallerSha256: D57DC3E1BA490AEE856C28B4915D09E3F49442461E46E481BC6B2D18207831D7
+ManifestType: installer
+ManifestVersion: 1.0.0
+
diff --git a/manifests/p/Python/Python/2/2.7.16/Python.Python.2.locale.en-US.yaml b/manifests/p/Python/Python/2/2.7.16/Python.Python.2.locale.en-US.yaml
new file mode 100644
index 000000000..09f735f0a
--- /dev/null
+++ b/manifests/p/Python/Python/2/2.7.16/Python.Python.2.locale.en-US.yaml
@@ -0,0 +1,20 @@
+# yaml-language-server: $schema=https://aka.ms/winget-manifest.defaultLocale.1.0.0.schema.json
+PackageIdentifier: Python.Python.2
+PackageVersion: 2.7.16
+PackageLocale: en-US
+Author: Python
+Tags:
+- python
+- python3
+- programming language
+- script
+- glue language
+PackageUrl: https://www.python.org
+LicenseUrl: https://docs.python.org/3/license.html
+Publisher: Python
+PackageName: Python 2.7.16
+License: PSF LICENSE AGREEMENT FOR PYTHON
+ShortDescription: Python is a programming language that lets you work more quickly and integrate your systems more effectively.
+ManifestType: defaultLocale
+ManifestVersion: 1.0.0
+
diff --git a/manifests/p/Python/Python/2/2.7.16/Python.Python.2.yaml b/manifests/p/Python/Python/2/2.7.16/Python.Python.2.yaml
new file mode 100644
index 000000000..0e36c89ad
--- /dev/null
+++ b/manifests/p/Python/Python/2/2.7.16/Python.Python.2.yaml
@@ -0,0 +1,7 @@
+# yaml-language-server: $schema=https://aka.ms/winget-manifest.version.1.0.0.schema.json
+PackageIdentifier: Python.Python.2
+PackageVersion: 2.7.16
+DefaultLocale: en-US
+ManifestType: version
+ManifestVersion: 1.0.0
+