diff --git a/src/openrct2-ui/drawing/engines/opengl/OpenGLAPI.h b/src/openrct2-ui/drawing/engines/opengl/OpenGLAPI.h
index ded0e1dc03..dd9a3f1370 100644
--- a/src/openrct2-ui/drawing/engines/opengl/OpenGLAPI.h
+++ b/src/openrct2-ui/drawing/engines/opengl/OpenGLAPI.h
@@ -42,8 +42,10 @@
 #endif
 
 #include <SDL_opengl.h>
-// OpenRCT2: SDL_opengl.h includes windows.h, which defines the CreateWindow macro and causes conflicts
+// OpenRCT2: SDL_opengl.h includes windows.h, which defines some macros that can cause conflicts
 #undef CreateWindow
+#undef CreateDirectory
+#undef GetMessage
 
 #ifdef OPENGL_NO_LINK
 
diff --git a/src/openrct2/core/FileStream.hpp b/src/openrct2/core/FileStream.hpp
index c683f84401..529fd41e90 100644
--- a/src/openrct2/core/FileStream.hpp
+++ b/src/openrct2/core/FileStream.hpp
@@ -12,6 +12,7 @@
 #include "../common.h"
 #include "../localisation/Language.h"
 #include "IStream.hpp"
+#include "Path.hpp"
 #include "String.hpp"
 
 #include <algorithm>
@@ -81,6 +82,16 @@ namespace OpenRCT2
                     throw;
             }
 
+            // Make sure the directory exists before writing to a file inside it
+            if (_canWrite)
+            {
+                std::string directory = Path::GetDirectory(path);
+                if (!Path::DirectoryExists(directory))
+                {
+                    Path::CreateDirectory(directory);
+                }
+            }
+
 #ifdef _WIN32
             auto pathW = String::ToWideChar(path);
             auto modeW = String::ToWideChar(mode);