diff --git a/.env b/.env
index 6d64d284780..6f830ca229b 100644
--- a/.env
+++ b/.env
@@ -102,8 +102,8 @@ VCPKG="4334d8b4c8916018600212ab4dd4bbdc343065d1"    # 2025.09.17 Release
 # ci/docker/python-*-windows-*.dockerfile or the vcpkg config.
 # This is a workaround for our CI problem that "archery docker build" doesn't
 # use pulled built images in dev/tasks/python-wheels/github.windows.yml.
-PYTHON_WHEEL_WINDOWS_IMAGE_REVISION=2026-01-22
-PYTHON_WHEEL_WINDOWS_TEST_IMAGE_REVISION=2026-01-22
+PYTHON_WHEEL_WINDOWS_IMAGE_REVISION=2026-01-27
+PYTHON_WHEEL_WINDOWS_TEST_IMAGE_REVISION=2026-01-27
 
 # Use conanio/${CONAN_BASE}:{CONAN_VERSION} for "docker compose run --rm conan".
 # See https://github.com/conan-io/conan-docker-tools#readme and
diff --git a/ci/docker/python-free-threaded-wheel-windows-test-vs2022.dockerfile b/ci/docker/python-free-threaded-wheel-windows-test-vs2022.dockerfile
index ab257b271e5..0ffb08edf8f 100644
--- a/ci/docker/python-free-threaded-wheel-windows-test-vs2022.dockerfile
+++ b/ci/docker/python-free-threaded-wheel-windows-test-vs2022.dockerfile
@@ -26,18 +26,12 @@ FROM ${base}
 
 ARG python=3.13
 
-# hadolint ignore=SC1072
-RUN (if "%python%"=="3.13" setx PYTHON_VERSION "3.13.1") & \
-    (if "%python%"=="3.14" setx PYTHON_VERSION "3.14.0")
-
-SHELL ["powershell", "-NoProfile", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
-RUN $version = $env:PYTHON_VERSION; \
-    $filename = 'python-' + $version + '-amd64.exe'; \
-    $url = 'https://www.python.org/ftp/python/' + $version + '/' + $filename; \
-    Invoke-WebRequest -Uri $url -OutFile $filename; \
-    Start-Process -FilePath $filename -ArgumentList '/quiet', 'Include_freethreaded=1' -Wait
-
-ENV PYTHON_CMD="py -${python}t"
+ARG python_variant_suffix=""
+ENV PYTHON_VERSION=${python}${python_variant_suffix}
+
+RUN pymanager install %PYTHON_VERSION%
+
+ENV PYTHON_CMD="py -${python}${python_variant_suffix}"
 
 SHELL ["cmd", "/S", "/C"]
 RUN %PYTHON_CMD% -m pip install -U pip setuptools & \
diff --git a/ci/docker/python-wheel-windows-test-vs2022-base.dockerfile b/ci/docker/python-wheel-windows-test-vs2022-base.dockerfile
deleted file mode 100644
index bd1da7b14b3..00000000000
--- a/ci/docker/python-wheel-windows-test-vs2022-base.dockerfile
+++ /dev/null
@@ -1,65 +0,0 @@
-# escape=`
-
-# Licensed to the Apache Software Foundation (ASF) under one
-# or more contributor license agreements.  See the NOTICE file
-# distributed with this work for additional information
-# regarding copyright ownership.  The ASF licenses this file
-# to you under the Apache License, Version 2.0 (the
-# "License"); you may not use this file except in compliance
-# with the License.  You may obtain a copy of the License at
-#
-#   http://www.apache.org/licenses/LICENSE-2.0
-#
-# Unless required by applicable law or agreed to in writing,
-# software distributed under the License is distributed on an
-# "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
-# KIND, either express or implied.  See the License for the
-# specific language governing permissions and limitations
-# under the License.
-
-# NOTE: You must update PYTHON_WHEEL_WINDOWS_TEST_IMAGE_REVISION in .env
-# when you update this file.
-
-FROM mcr.microsoft.com/windows/servercore:ltsc2022
-
-# Ensure we in a command shell and not Powershell
-SHELL ["cmd", "/S", "/C"]
-
-# Install MSVC BuildTools
-#
-# The set of components below (lines starting with --add) is the most minimal
-# set we could find that would still compile Arrow C++.
-RUN `
-    curl -SL --output vs_buildtools.exe https://aka.ms/vs/17/release/vs_buildtools.exe `
-    && (start /w vs_buildtools.exe --quiet --wait --norestart --nocache `
-    --installPath "%ProgramFiles(x86)%\Microsoft Visual Studio\2022\BuildTools" `
-    --add Microsoft.VisualStudio.Component.VC.CoreBuildTools `
-    --add Microsoft.VisualStudio.Component.VC.Tools.x86.x64 `
-    --add Microsoft.VisualStudio.Component.Windows11SDK.26100 `
-    --add Microsoft.VisualStudio.Component.VC.CMake.Project `
-    || IF "%ERRORLEVEL%"=="3010" EXIT 0) `
-    && del /q vs_buildtools.exe
-
-# Install choco CLI
-#
-# We switch into Powershell just for this command and switch back to cmd
-# See https://chocolatey.org/install#completely-offline-install
-SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop'; $ProgressPreference = 'SilentlyContinue';"]
-RUN `
-    Set-ExecutionPolicy Bypass -Scope Process -Force; [System.Net.ServicePointManager]::SecurityProtocol = [System.Net.ServicePointManager]::SecurityProtocol -bor 3072; iex ((New-Object System.Net.WebClient).DownloadString('https://community.chocolatey.org/install.ps1'))
-SHELL ["cmd", "/S", "/C"]
-
-# Install git, wget, minio
-RUN choco install --no-progress -r -y git wget
-RUN curl https://dl.min.io/server/minio/release/windows-amd64/archive/minio.RELEASE.2025-01-20T14-49-07Z `
-    --output "C:\Windows\Minio.exe"
-
-# Install the GCS testbench using a well-known Python version.
-# NOTE: cannot use pipx's `--fetch-missing-python` because of
-# https://github.com/pypa/pipx/issues/1521, therefore download Python ourselves.
-RUN choco install -r -y --pre --no-progress python --version=3.11.9
-ENV PIPX_BIN_DIR=C:\\Windows\\
-ENV PIPX_PYTHON="C:\Python311\python.exe"
-COPY ci/scripts/install_gcs_testbench.bat C:/arrow/ci/scripts/
-RUN call "C:\arrow\ci\scripts\install_gcs_testbench.bat" && `
-    storage-testbench -h
diff --git a/ci/docker/python-wheel-windows-test-vs2022.dockerfile b/ci/docker/python-wheel-windows-test-vs2022.dockerfile
index 73a9e167fea..5a5bf1506a6 100644
--- a/ci/docker/python-wheel-windows-test-vs2022.dockerfile
+++ b/ci/docker/python-wheel-windows-test-vs2022.dockerfile
@@ -26,16 +26,15 @@ FROM ${base}
 
 # hadolint shell=cmd.exe
 
-# Define the full version number otherwise choco falls back to patch number 0 (3.10 => 3.10.0)
 ARG python=3.10
-RUN (if "%python%"=="3.10" setx PYTHON_VERSION "3.10.11" && setx PYTHON_CMD "py -3.10") & \
-    (if "%python%"=="3.11" setx PYTHON_VERSION "3.11.9" && setx PYTHON_CMD "py -3.11") & \
-    (if "%python%"=="3.12" setx PYTHON_VERSION "3.12.10" && setx PYTHON_CMD "py -3.12") & \
-    (if "%python%"=="3.13" setx PYTHON_VERSION "3.13.9" && setx PYTHON_CMD "py -3.13") & \
-    (if "%python%"=="3.14" setx PYTHON_VERSION "3.14.0" && setx PYTHON_CMD "py -3.14")
 
-# hadolint ignore=DL3059
-RUN choco install -r -y --pre --no-progress --force python --version=%PYTHON_VERSION%
+ARG python_variant_suffix=""
+ENV PYTHON_VERSION=${python}${python_variant_suffix}
+
+RUN pymanager install %PYTHON_VERSION%
+
+ENV PYTHON_CMD="py -${python}${python_variant_suffix}"
+
 # hadolint ignore=DL3059
 RUN %PYTHON_CMD% -m pip install -U pip setuptools
 
diff --git a/ci/docker/python-wheel-windows-vs2022-base.dockerfile b/ci/docker/python-wheel-windows-vs2022-base.dockerfile
index 426286ebe07..1d53e863017 100644
--- a/ci/docker/python-wheel-windows-vs2022-base.dockerfile
+++ b/ci/docker/python-wheel-windows-vs2022-base.dockerfile
@@ -104,6 +104,21 @@ RUN choco install --no-progress -r -y git gzip ninja wget
 # Add UNIX tools to PATH
 RUN setx path "%path%;C:\Program Files\Git\usr\bin"
 
+# Install git, wget, minio
+RUN choco install --no-progress -r -y git wget
+RUN curl https://dl.min.io/server/minio/release/windows-amd64/archive/minio.RELEASE.2025-01-20T14-49-07Z `
+    --output "C:\Windows\Minio.exe"
+
+# Install the GCS testbench using a well-known Python version.
+# NOTE: cannot use pipx's `--fetch-missing-python` because of
+# https://github.com/pypa/pipx/issues/1521, therefore download Python ourselves.
+RUN choco install -r -y --pre --no-progress python --version=3.11.9
+ENV PIPX_BIN_DIR=C:\\Windows\\
+ENV PIPX_PYTHON="C:\Python311\python.exe"
+COPY ci/scripts/install_gcs_testbench.bat C:/arrow/ci/scripts/
+RUN call "C:\arrow\ci\scripts\install_gcs_testbench.bat" && `
+    storage-testbench -h
+
 # Install vcpkg
 #
 # Compiling vcpkg itself from a git tag doesn't work anymore since vcpkg has
diff --git a/ci/docker/python-wheel-windows-vs2022.dockerfile b/ci/docker/python-wheel-windows-vs2022.dockerfile
index e25ebef156c..0ed5be4939a 100644
--- a/ci/docker/python-wheel-windows-vs2022.dockerfile
+++ b/ci/docker/python-wheel-windows-vs2022.dockerfile
@@ -21,7 +21,6 @@
 ARG base
 FROM ${base}
 
-# Define the full version number otherwise choco falls back to patch number 0 (3.10 => 3.10.0)
 ARG python=3.10
 
 ARG python_variant_suffix=""
diff --git a/compose.yaml b/compose.yaml
index c99f19e35e0..3474643fe6e 100644
--- a/compose.yaml
+++ b/compose.yaml
@@ -178,7 +178,6 @@ x-hierarchy:
   - python-wheel-windows-vs2022-base:
     - python-wheel-windows-vs2022
     - python-free-threaded-wheel-windows-vs2022
-  - python-wheel-windows-test-base:
     - python-wheel-windows-test
     - python-free-threaded-wheel-windows-test
 
@@ -1416,18 +1415,11 @@ services:
     volumes: *python-wheel-windows-vs2022-volumes
     command: arrow\\ci\\scripts\\python_wheel_windows_build.bat
 
-  python-wheel-windows-test-base:
-    image: ${REPO}:python-wheel-windows-test-vs2022-base-${PYTHON_WHEEL_WINDOWS_TEST_IMAGE_REVISION}
-    build:
-      context: .
-      dockerfile: ci/docker/python-wheel-windows-test-vs2022-base.dockerfile
-    volumes: *python-wheel-windows-vs2022-volumes
-
   python-wheel-windows-test:
     image: ${REPO}:python-${PYTHON}-wheel-windows-test-vs2022-${PYTHON_WHEEL_WINDOWS_TEST_IMAGE_REVISION}
     build:
       args:
-        base: ${REPO}:python-wheel-windows-test-vs2022-base-${PYTHON_WHEEL_WINDOWS_TEST_IMAGE_REVISION}
+        base: ${REPO}:python-wheel-windows-vs2022-base-vcpkg-${VCPKG}-${PYTHON_WHEEL_WINDOWS_IMAGE_REVISION}
         python: ${PYTHON}
       context: .
       dockerfile: ci/docker/python-wheel-windows-test-vs2022.dockerfile
@@ -1438,8 +1430,9 @@ services:
     image: ${REPO}:python-${PYTHON}-free-threaded-wheel-windows-test-vs2022-${PYTHON_WHEEL_WINDOWS_TEST_IMAGE_REVISION}
     build:
       args:
-        base: ${REPO}:python-wheel-windows-test-vs2022-base-${PYTHON_WHEEL_WINDOWS_TEST_IMAGE_REVISION}
+        base: ${REPO}:python-wheel-windows-vs2022-base-vcpkg-${VCPKG}-${PYTHON_WHEEL_WINDOWS_IMAGE_REVISION}
         python: ${PYTHON}
+        python_variant_suffix: t
       context: .
       dockerfile: ci/docker/python-free-threaded-wheel-windows-test-vs2022.dockerfile
     volumes: *python-wheel-windows-vs2022-volumes