diff --git a/.ci/openvino-onnx/Dockerfile b/.ci/openvino-onnx/Dockerfile
index ef7663a03ce92a..d5439a3c5e1901 100644
--- a/.ci/openvino-onnx/Dockerfile
+++ b/.ci/openvino-onnx/Dockerfile
@@ -40,16 +40,11 @@ RUN apt-get update && apt-get -y --no-install-recommends install \
         python3-dev \
         pybind11-dev \
         python3-virtualenv \
-        python3-venv \
+        cython3 \
         tox && \
     apt-get clean autoclean && \
     apt-get autoremove -y
 
-RUN python3 -m venv ~/.venv
-RUN . ~/.venv/bin/activate
-RUN which python3
-RUN python3 -m pip install "cython>=3.0.0" --break-system-packages
-
 # Build OpenVINO
 COPY . /openvino/
 WORKDIR /openvino/build
@@ -70,8 +65,7 @@ RUN cmake .. \
     -DENABLE_OV_PYTORCH_FRONTEND=ON \
     -DENABLE_OV_TF_FRONTEND=OFF \
     -DENABLE_OPENVINO_DEBUG=OFF \
-    -DCMAKE_INSTALL_PREFIX=/openvino/dist \
-    -DPYTHON_EXECUTABLE=`which python3`
+    -DCMAKE_INSTALL_PREFIX=/openvino/dist
 RUN ninja install
 
 # Run tests via tox
diff --git a/docs/requirements.txt b/docs/requirements.txt
index 834c1aafbf92b9..10f970b6268452 100644
--- a/docs/requirements.txt
+++ b/docs/requirements.txt
@@ -5,7 +5,7 @@ Babel==2.11.0
 beautifulsoup4==4.9.3
 certifi==2023.7.22
 colorama==0.4.6
-Cython==3.0.2
+Cython==0.29.33
 docutils==0.16
 idna==3.4
 imagesize==1.2.0
diff --git a/src/bindings/python/src/compatibility/openvino/CMakeLists.txt b/src/bindings/python/src/compatibility/openvino/CMakeLists.txt
index 5b7d2efa4b8356..6a1c48777cfa70 100644
--- a/src/bindings/python/src/compatibility/openvino/CMakeLists.txt
+++ b/src/bindings/python/src/compatibility/openvino/CMakeLists.txt
@@ -21,13 +21,11 @@ endif()
 
 include (cmake/UseCython.cmake)
 
-# TODO: Reenable once Windows issue is resolved
-# # Check Cython version
-# if(CYTHON_VERSION VERSION_LESS "3.0.0")
-#     message(FATAL_ERROR "OpenVINO Python API needs at least Cython version 3.0.0, found version ${CYTHON_VERSION}")
-# else()
-#     message(STATUS "Found Cython version ${CYTHON_VERSION}")
-# endif()
+if(CYTHON_VERSION VERSION_LESS 0.29)
+    message(FATAL_ERROR "OpenVINO Python API needs at least Cython version 0.29, found version ${CYTHON_VERSION}")
+else()
+    message(STATUS "Found Cython version ${CYTHON_VERSION}")
+endif()
 
 set(pyversion python${PYTHON_VERSION_MAJOR}.${PYTHON_VERSION_MINOR})
 
diff --git a/src/bindings/python/src/compatibility/openvino/cmake/CythonConfig.cmake b/src/bindings/python/src/compatibility/openvino/cmake/CythonConfig.cmake
index 8129313410c76c..4cc32dacec1375 100644
--- a/src/bindings/python/src/compatibility/openvino/cmake/CythonConfig.cmake
+++ b/src/bindings/python/src/compatibility/openvino/cmake/CythonConfig.cmake
@@ -50,7 +50,30 @@ include( FindPackageHandleStandardArgs )
 FIND_PACKAGE_HANDLE_STANDARD_ARGS( Cython REQUIRED_VARS CYTHON_EXECUTABLE )
 
 # Find Cython version
-execute_process(COMMAND ${CYTHON_EXECUTABLE} -V ERROR_VARIABLE CYTHON_OUTPUT)
-string(REGEX REPLACE "^Cython version ([0-9]+\\.[0-9]+(\\.[0-9]+)?).*" "\\1" CYTHON_VERSION "${CYTHON_OUTPUT}")
+execute_process(COMMAND ${CYTHON_EXECUTABLE} -V
+  ERROR_VARIABLE CYTHON_OUTPUT
+  OUTPUT_VARIABLE CYTHON_ERROR_MESSAGE
+  RESULT_VARIABLE CYTHON_EXIT_CODE
+  OUTPUT_STRIP_TRAILING_WHITESPACE)
+
+if(CYTHON_EXIT_CODE EQUAL 0)
+  if(NOT CYTHON_OUTPUT)
+    set(CYTHON_OUTPUT "${CYTHON_ERROR_MESSAGE}")
+  endif()
+  string(REGEX REPLACE "^Cython version ([0-9]+\\.[0-9]+(\\.[0-9]+)?).*" "\\1" CYTHON_VERSION "${CYTHON_OUTPUT}")
+else()
+  if(${CMAKE_FIND_PACKAGE_NAME}_FIND_QUIETLY)
+      set(CYTHON_MESSAGE_MODE TRACE)
+  endif()
+  if(${CMAKE_FIND_PACKAGE_NAME}_FIND_REQUIRED)
+      set(CYTHON_MESSAGE_MODE FATAL_ERROR)
+  endif()
+  message(${CYTHON_MESSAGE_MODE} "Failed to detect cython version: ${CYTHON_ERROR_MESSAGE}")
+  unset(CYTHON_MESSAGE_MODE)
+endif()
+
+unset(CYTHON_OUTPUT)
+unset(CYTHON_EXIT_CODE)
+unset(CYTHON_ERROR_MESSAGE)
 
 mark_as_advanced( CYTHON_EXECUTABLE CYTHON_VERSION )
diff --git a/src/bindings/python/src/compatibility/openvino/requirements-dev.txt b/src/bindings/python/src/compatibility/openvino/requirements-dev.txt
index 8b4d6888dcb55e..aca50982d0dc53 100644
--- a/src/bindings/python/src/compatibility/openvino/requirements-dev.txt
+++ b/src/bindings/python/src/compatibility/openvino/requirements-dev.txt
@@ -1 +1 @@
-Cython>=3.0.0
+cython>=0.29.32