I had no issues using:

• Windows XP
• Activestate 5.10.0
• MinGW 3.4.2 (comes with Bloodshed Dev-Cpp)
• 'ppm install dmake'

I downloaded the Tk module from CPAN and just did the

perl Makefile.PL
dmake
dmake test
dmake install
[download]

No issues.

I've since switched to Strawberry Perl 5.12.2 on Windows XP following the same download and manual build for Tk and had no issues. Note that Strawberry was using its own gcc compiler (I believe version 4.4.3).

UPDATE: I tried this on Windows 7 x64 (Strawberry Perl 5.12.3) and got some serious errors at the 'dmake' step. I found this link:

http://www.nntp.perl.org/group/perl.win32.vanilla/2010/07/msg252.html

Which basically gives this advice. Go to the downloaded working CPAN directory of Tk and 'cd pTk\mTk\xlib\X11' and edit the file 'X.h'.

Starting at 43:
43: #ifdef _DWIN64
44: typedef __int64 XID;
45: #else
46: typedef unsigned long XID;
47: #endif
 
I was able to correct this by changing this to
43: #ifdef _DWIN64
44: #include <inttypes.h>
45: typedef __int64 XID;
46: #else
47: typedef unsigned long XID;
48: #endif
[download]

Change back to the working CPAN directory of Tk (cd ..\..\..\..) and run 'dmake'. It should work now. You can follow with 'dmake test' and 'dmake install'.