Although org doesn't have the feature you are asking for, I have the following in my configuration that you may find useful:
#+begin_src emacs-lisp (font-lock-add-keywords 'org-mode `(("^[ \t]*\\(?:[-+*]\\|[0-9]+[).]\\)[ \t]+\\(\\(?:\\[@\\(?:start:\\)?[0-9]+\\][ \t]*\\)?\\[\\(?:X\\|\\([0-9]+\\)/\\2\\)\\][^\n]*\n\\)" 1 'org-headline-done prepend)) 'append) #+end_src -- : Eric S Fraga, with org release_9.6.6-418-g294a4d in Emacs 30.0.50