I have the same problem.

I have the following files in my site-lisp folder:

C:\emacs\site-lisp\find-recursive.el
C:\emacs\site-lisp\psvn.el
C:\emacs\site-lisp\snippet.el
C:\emacs\site-lisp\subdirs.el
C:\emacs\site-lisp\emacs-rails\ChangeLog
C:\emacs\site-lisp\emacs-rails\rails-core.el
C:\emacs\site-lisp\emacs-rails\rails-for-controller.el
C:\emacs\site-lisp\emacs-rails\rails-for-layout.el
C:\emacs\site-lisp\emacs-rails\rails-for-rhtml.el
C:\emacs\site-lisp\emacs-rails\rails-lib.el
C:\emacs\site-lisp\emacs-rails\rails-navigation.el
C:\emacs\site-lisp\emacs-rails\rails-ruby.el
C:\emacs\site-lisp\emacs-rails\rails-scripts.el
C:\emacs\site-lisp\emacs-rails\rails-ui.el
C:\emacs\site-lisp\emacs-rails\rails-webrick.el
C:\emacs\site-lisp\emacs-rails\rails.el
C:\emacs\site-lisp\emacs-rails\README
C:\emacs\site-lisp\ruby\inf-ruby.el
C:\emacs\site-lisp\ruby\README
C:\emacs\site-lisp\ruby\ruby-electric.el
C:\emacs\site-lisp\ruby\ruby-mode.el
C:\emacs\site-lisp\ruby\rubydb2x.el
C:\emacs\site-lisp\ruby\rubydb3x.el

And here is my .emacs file:

(custom-set-variables
  ;; custom-set-variables was added by Custom.
  ;; If you edit it by hand, you could mess it up, so be careful.
  ;; Your init file should contain only one such instance.
  ;; If there is more than one, they won't work right.
 '(cua-mode t nil (cua-base))
 '(debug-on-error t)
 '(global-font-lock-mode t nil (font-core))
 '(show-paren-mode nil)
 '(transient-mark-mode t))
(custom-set-faces
  ;; custom-set-faces was added by Custom.
  ;; If you edit it by hand, you could mess it up, so be careful.
  ;; Your init file should contain only one such instance.
  ;; If there is more than one, they won't work right.
 )

  ;;(autoload 'ruby-mode "ruby-mode" "Load ruby-mode")
  ;;(add-to-list 'auto-mode-alist '("\\.rb$" . ruby-mode))
  ;; uncomment the next line if you want syntax highlighting
  ;;(add-hook 'ruby-mode-hook 'turn-on-font-lock)

    (defun try-complete-abbrev (old)
   (if (expand-abbrev) t nil))

  (setq hippie-expand-try-functions-list
       '(try-complete-abbrev
         try-complete-file-name
         try-expand-dabbrev))

  (require 'rails)

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