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My current list of changed_files() (command from the code)
% hg status --added --modified --no-status
Lib\idlelib\RstripExtension.py
Misc\ACKS
Misc\NEWS
Lib\idlelib\idle_test\mock_idle.py
Lib\idlelib\idle_test\test_rstrip.py
but
F:\Python\dev\py33>pcbuild\python_d tools/scripts/patchcheck.py
...
Misc/ACKS updated ... NO
Misc/NEWS updated ... NO
The problem is that 'Misc/ACKs' is not in the list, even though 'Misc\ACKS' is ;-(.
One possible fix is to conditionally change '\' to '/' in the file list, or maybe just in special_files, as that seems to be the only category affected.
Another is to change line 156 (3.3) from
 special_files = {'Misc/ACKS', 'Misc/NEWS'} & set(file_paths)
to
 special_files = {'Misc/ACKS', 'Misc/NEWS', 'Misc\ACKS', Misc\NEWS'} & set(file_paths).
A third is to check for both versions in credit_given() (125) and reported_news() (131).
I don't know if there is an issue with Macs or not.

Using os.path.join to create the filenames should also work, I would think.

Ronald or Ned, is the attached patch OK for Macs?

Re the patch: it looks like there's a debugging print left in it. (Also, FYI, the patch did not apply cleanly using normal Unix patch; I had to strip the \r characters with (tr -d '\r' <patchcheck.diff); also it's best to not include Misc/NEWS changes in uploaded patches.) Otherwise, it should be good to go.
In general from Python's perspective, OS X is a POSIX-compliant (e.g. Unix-y) system, with "normal" Unix file system syntax and BSD-ish semantics. So there's nothing special about os.path manipulations functions on OS X (platform="darwin") vs other Unix-based systems. What can be confusing is that Classic Mac OS (Mac OS 9 and earlier) was not a Unix-based system and had a totally different file syntax. Classic Mac OS has been obsolete for over a decade and nearly all traces of support for it (platform="mac") have been removed from Python 3 and Python 2.7, other than in os.path.

Sorry, I forgot to paste the patch diff into Notepad++ rather than Idle in order to save it without \r. (That would be a useful option for Idle too.) Good to know that I can forget about Classic Mac. I deleted the debug print.

New changeset 26686d227e41 by Terry Jan Reedy in branch '3.3':
Issue #18439: Make patchcheck work on Windows for ACKS, NEWS.
http://hg.python.org/cpython/rev/26686d227e41
New changeset 13950a33f889 by Terry Jan Reedy in branch '2.7':
Issue #18439: Make patchcheck work on Windows for ACKS, NEWS.
http://hg.python.org/cpython/rev/13950a33f889
New changeset f737673e909b by Terry Jan Reedy in branch '2.7':
Issue #18439: Move news entry misplaced by graft merge.
http://hg.python.org/cpython/rev/f737673e909b