I'm not sure where the file command comes from. Anyway the size/datetime....

06/06/2015  06:17           181,880 tcl86.lib
[download]

I downloaded an sha1sum.exe, here's the result

5b2c87ccbc0838d7c9687f15f5ab6a33f7f77837  C:\Tcl\lib\tcl86.lib
[download]

and the results of objdumo

C:\Tcl\lib>objdump -p "C:\Tcl\lib\tcl86.lib" |head
In archive C:\Tcl\lib\tcl86.lib:

tcl86.dll:     file format pe-x86-64

Characteristics 0x0

Time/Date               Sat Jun 06 05:37:55 2015
Magic                   0000
MajorLinkerVersion      0
MinorLinkerVersion      0
[download]

I appreciate your help

Hmm, thats kinda interesting :)

Ok next step is do what syphilis suggested which is generate a new "lib" from the dll( HOWTO Create an Import Library for a DLL using MinGW | MinGW )

So start a new shell and run

 
chdir C:\Tcl\lib
move tcl86.lib  original-tcl86.lib 

gendef  C:\Tcl\bin\tcl86.dll
dlltool --kill-at --input-def tcl86.def --output-lib tcl86.lib
[download]

Then back in the the other cmd window run dmake again

If it doesn't work copy/paste the error to share with us here :)

Then try again with     dlltool -z tcl86.def --export-all-symbol C:\Tcl\bin\tcl86.dll instead of gendef

Thanks for this guidance. Made a little progress, but still could use your help. The commands you suggested worked without error....

C:\Tcl\lib>move tcl86.lib  original-tcl86.lib
        1 file(s) moved.

C:\Tcl\lib>gendef  C:\Tcl\bin\tcl86.dll
 * [C:\Tcl\bin\tcl86.dll] Found PE+ image

C:\Tcl\lib>dlltool --kill-at --input-def tcl86.def --output-lib tcl86.
+lib

C:\Tcl\lib>
[download]

I was able to dmake the Tcl package without error. However when I tried to test I got the following for each test (including just one to save your eyes).

C:\STRAWB~1\cpan\build\Tcl-1.02-DZAeQs>dmake test
"C:\Strawberry\perl\bin\perl.exe" "-MExtUtils::Command::MM" "-MTest::H
+arness" "-e" "undef *Test::Harness::Switches; test_harness(0, 'blib\l
+ib', 'blib\arch')" t/
*.t
t/call.t ........... Can't load 'C:\STRAWB~1\cpan\build\Tcl-1.02-DZAeQ
+s\blib\arch/auto/Tcl/Tcl.xs.dll' for module Tcl: load_file:The specif
+ied procedure could not be found at C:/Strawberry/perl/lib/DynaLoader
+.pm line 193.
  at t/call.t line 6.
Compilation failed in require at t/call.t line 6.
BEGIN failed--compilation aborted at t/call.t line 6.
t/call.t ........... Dubious, test returned 255 (wstat 65280, 0xff00)
No subtests run
[download]

In addition I was presented with the windows error message "The procedure entry point inflateGetHeader could not be located in the dynamic link library zlib1.dll"

zlib1.dll is included in c:\Tcl\bin, but without a corresponding library in c:\Tcl\lib

I ran the following code to create the symbol list from zlib1.dll, and indeed the symmbol inflateGetHeader is included in zlib1.def. I also created libzlib1.a

C:\Tcl\lib>gendef  C:\Tcl\bin\zlib1.dll
 * [C:\Tcl\bin\zlib1.dll] Found PE+ image

C:\Tcl\lib>dlltool --kill-at --input-def zlib1.def --output-lib zlib1.
+lib

C:\Tcl\lib>
[download]

I then went through dmake clean, perl Malefile.PL, dmake and dmake test again. Same result.

I also tried adding libzlib1.a as an additional library in the makefile so that the output from perl Makefile.pl is

tclsh=C:/Tcl/bin/tclsh.exe
tclConfig.sh=C:/Tcl/lib/tclConfig.sh
tcl_library=C:/Tcl/lib/tcl8.6
tcl_version=8.6
LIBS   = -LC:/Tcl/lib -ltcl86 -lzlib1
INC    = -IC:/Tcl/include
DEFINE =
Checking if your kit is complete...
Looks good
Generating a dmake-style Makefile
Writing Makefile for Tcl
Writing MYMETA.yml and MYMETA.json
[download]

I repeated the dmake and test again, but with same results. Any recommendations on my next steps?