Hmm, I think I have an older ruby, but most of my gems are newer:

fxri (0.3.6)
fxruby (1.6.12)
hpricot (0.6)
log4r (1.0.5)
rake (0.7.3)
rubyscript2exe (0.5.3)
sources (0.0.1)
sqlite3-ruby (1.2.3)
win32-api (1.4.3, 1.0.4)
win32-clipboard (0.4.3)
win32-dir (0.3.2)
win32-eventlog (0.4.6)
win32-file (0.5.4)
win32-file-stat (1.2.7)
win32-open3 (0.3.1)
win32-process (0.6.0, 0.5.3)
win32-sapi (0.1.4)
win32-sound (0.4.1)
windows-api (0.3.0, 0.2.0)
windows-pr (1.0.5, 0.7.2)

ruby -v
ruby 1.8.6 (2007-09-24 patchlevel 111) [i386-mswin32]

Can you try "gem update" and installing newer mswin32 versions? Wonder why your gems differ.