diff --git a/.github/docker/windows/Dockerfile b/.github/docker/windows/Dockerfile
index 4f13814a8..5cefc53d1 100644
--- a/.github/docker/windows/Dockerfile
+++ b/.github/docker/windows/Dockerfile
@@ -5,6 +5,13 @@ FROM mcr.microsoft.com/windows/servercore:1809-amd64
 
 SHELL ["powershell.exe", "-NoLogo", "-NoProfile", "-ExecutionPolicy", "ByPass"]
 
+# List of Python versions to install (with ; as delimiter)
+# For example: 2.7.5;3.7.5
+#
+ARG PYTHON_VERSIONS
+
+RUN echo ${ENV:PYTHON_VERSIONS}
+
 # ------------------------------------------------------------------------------------------------------------
 # Chocolatey
 #
@@ -22,6 +29,15 @@ RUN choco install git.install --yes --version=2.23.0
 #
 RUN choco install cmake --yes --version=3.15.4 --installargs 'ADD_CMAKE_TO_PATH=System'
 
+# ------------------------------------------------------------------------------------------------------------
+# Python
+#
+RUN (${ENV:PYTHON_VERSIONS}).Split(";") | ForEach-Object {                                                                                   \
+    ${PYTHON_VERSION} = $_                                                                                                                  \
+    ${PYTHON_VERSION_CODE} += ( $PYTHON_VERSION.Split(".")[0..1] -Join '' )                                                                             \
+    choco install python --yes --version=${PYTHON_VERSION} --installargs='TargetDir=""C:\python${PYTHON_VERSION_CODE}"" CompileAll=""1" Shortcuts=0'    \
+}
+
 # ------------------------------------------------------------------------------------------------------------
 # pwsh (PowerShellCore)
 #
diff --git a/.github/workflows/windows-docker-image.yaml b/.github/workflows/windows-docker-image.yaml
index 6c4c3e281..cd8b26acb 100644
--- a/.github/workflows/windows-docker-image.yaml
+++ b/.github/workflows/windows-docker-image.yaml
@@ -30,6 +30,7 @@ jobs:
     runs-on: windows-2019
 
     steps:
+
       - name: Login to docker repository
         run: |
           ${gh_user} = ("${{ github.repository }}" -Split '/')[0]
@@ -42,5 +43,9 @@ jobs:
           ${gh_user} = ("${{ github.repository }}" -Split '/')[0]
 
           cd .github\docker\windows
-          docker build --tag ${gh_user}/rez-test-win:${ENV:DOCKER_TAG} .
+          echo docker build --tag ${gh_user}/rez-test-win:${ENV:DOCKER_TAG} --build-arg PYTHON_VERSIONS=${ENV:PYTHON_VERSIONS} .
+          docker build --tag ${gh_user}/rez-test-win:${ENV:DOCKER_TAG} --build-arg PYTHON_VERSIONS=${ENV:PYTHON_VERSIONS} .
           docker push ${gh_user}/rez-test-win:${ENV:DOCKER_TAG}
+        env:
+          # Must match strategy in windows-docker.yaml
+          PYTHON_VERSIONS: '2.7.11;3.6.8;3.7.5'