diff --git a/.appveyor.yml b/.appveyor.yml
index 9419a1823..086d68859 100644
--- a/.appveyor.yml
+++ b/.appveyor.yml
@@ -7,8 +7,6 @@ environment:
       variant: windowsservercore-ltsc2016
     - version: 3.6
       variant: windowsservercore-ltsc2016
-    - version: 3.5
-      variant: windowsservercore-ltsc2016
     - version: 2.7
       variant: windowsservercore-ltsc2016
 
diff --git a/3.5/windows/windowsservercore-1709/Dockerfile b/3.5/windows/windowsservercore-1709/Dockerfile
deleted file mode 100644
index 6450aa9a8..000000000
--- a/3.5/windows/windowsservercore-1709/Dockerfile
+++ /dev/null
@@ -1,61 +0,0 @@
-#
-# NOTE: THIS DOCKERFILE IS GENERATED VIA "update.sh"
-#
-# PLEASE DO NOT EDIT IT DIRECTLY.
-#
-
-FROM microsoft/windowsservercore:1709
-
-SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
-
-ENV PYTHON_VERSION 3.5.5
-ENV PYTHON_RELEASE 3.5.5
-
-RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f $env:PYTHON_RELEASE, $env:PYTHON_VERSION); \
-	Write-Host ('Downloading {0} ...' -f $url); \
-	Invoke-WebRequest -Uri $url -OutFile 'python.exe'; \
-	\
-	Write-Host 'Installing ...'; \
-# https://docs.python.org/3.5/using/windows.html#installing-without-ui
-	Start-Process python.exe -Wait \
-		-ArgumentList @( \
-			'/quiet', \
-			'InstallAllUsers=1', \
-			'TargetDir=C:\Python', \
-			'PrependPath=1', \
-			'Shortcuts=0', \
-			'Include_doc=0', \
-			'Include_pip=0', \
-			'Include_test=0' \
-		); \
-	\
-# the installer updated PATH, so we should refresh our local value
-	$env:PATH = [Environment]::GetEnvironmentVariable('PATH', [EnvironmentVariableTarget]::Machine); \
-	\
-	Write-Host 'Verifying install ...'; \
-	Write-Host '  python --version'; python --version; \
-	\
-	Write-Host 'Removing ...'; \
-	Remove-Item python.exe -Force; \
-	\
-	Write-Host 'Complete.';
-
-# if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 9.0.1
-
-RUN Write-Host ('Installing pip=={0} ...' -f $env:PYTHON_PIP_VERSION); \
-	[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12; \
-	Invoke-WebRequest -Uri 'https://bootstrap.pypa.io/get-pip.py' -OutFile 'get-pip.py'; \
-	python get-pip.py \
-		--disable-pip-version-check \
-		--no-cache-dir \
-		('pip=={0}' -f $env:PYTHON_PIP_VERSION) \
-	; \
-	Remove-Item get-pip.py -Force; \
-	\
-	Write-Host 'Verifying pip install ...'; \
-	pip --version; \
-	\
-	Write-Host 'Complete.';
-
-CMD ["python"]
diff --git a/3.5/windows/windowsservercore-ltsc2016/Dockerfile b/3.5/windows/windowsservercore-ltsc2016/Dockerfile
deleted file mode 100644
index f84624d72..000000000
--- a/3.5/windows/windowsservercore-ltsc2016/Dockerfile
+++ /dev/null
@@ -1,61 +0,0 @@
-#
-# NOTE: THIS DOCKERFILE IS GENERATED VIA "update.sh"
-#
-# PLEASE DO NOT EDIT IT DIRECTLY.
-#
-
-FROM microsoft/windowsservercore:ltsc2016
-
-SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
-
-ENV PYTHON_VERSION 3.5.5
-ENV PYTHON_RELEASE 3.5.5
-
-RUN $url = ('https://www.python.org/ftp/python/{0}/python-{1}-amd64.exe' -f $env:PYTHON_RELEASE, $env:PYTHON_VERSION); \
-	Write-Host ('Downloading {0} ...' -f $url); \
-	Invoke-WebRequest -Uri $url -OutFile 'python.exe'; \
-	\
-	Write-Host 'Installing ...'; \
-# https://docs.python.org/3.5/using/windows.html#installing-without-ui
-	Start-Process python.exe -Wait \
-		-ArgumentList @( \
-			'/quiet', \
-			'InstallAllUsers=1', \
-			'TargetDir=C:\Python', \
-			'PrependPath=1', \
-			'Shortcuts=0', \
-			'Include_doc=0', \
-			'Include_pip=0', \
-			'Include_test=0' \
-		); \
-	\
-# the installer updated PATH, so we should refresh our local value
-	$env:PATH = [Environment]::GetEnvironmentVariable('PATH', [EnvironmentVariableTarget]::Machine); \
-	\
-	Write-Host 'Verifying install ...'; \
-	Write-Host '  python --version'; python --version; \
-	\
-	Write-Host 'Removing ...'; \
-	Remove-Item python.exe -Force; \
-	\
-	Write-Host 'Complete.';
-
-# if this is called "PIP_VERSION", pip explodes with "ValueError: invalid truth value '<VERSION>'"
-ENV PYTHON_PIP_VERSION 9.0.1
-
-RUN Write-Host ('Installing pip=={0} ...' -f $env:PYTHON_PIP_VERSION); \
-	[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12; \
-	Invoke-WebRequest -Uri 'https://bootstrap.pypa.io/get-pip.py' -OutFile 'get-pip.py'; \
-	python get-pip.py \
-		--disable-pip-version-check \
-		--no-cache-dir \
-		('pip=={0}' -f $env:PYTHON_PIP_VERSION) \
-	; \
-	Remove-Item get-pip.py -Force; \
-	\
-	Write-Host 'Verifying pip install ...'; \
-	pip --version; \
-	\
-	Write-Host 'Complete.';
-
-CMD ["python"]