Just for you, flip26, I went through my secondaries folder on my flash drive, and based on the completed secondary PDFs that I have (which is not all of the schools I applied to), I found the ones that do ask some kind of question related to what you're asking.
Albert Einstein: asks if you have applied previously to medical school at all, and also asks you to list all of the schools you've applied to in the past (wtf).
Columbia: asks if you've applied to P&S before and when. Also wants to know if you are sending new/updated recommendations.
Jefferson: asks if you've applied previously, and when.
Mount Sinai: Asks if you've applied to other med schools in past years, and if you've also applied to MSSM, asks for an explanation about it.
Penn State: Asks if you applied to PSU before (if yes, when, and did you get an interview? Also, asks how your qualifications have changed since then), asks if you've applied in the past to OTHER schools (when and how your qualifications have changed since then) AND also asks if you have MATRICULATED at any medical or professional school (if yes, provide name of institution, years attended and degree).
USC Keck: asks if you are reapplying to medical school (y/n), and asks if you are reapplying to Keck (y/n)
Yale: Asks if you've applied to Yale before, and if yes, what year.
Hope this gives you an idea of what to expect.