How to parse string dates with 2-digit year?

Prepend the century to your date using your own pivot:

  year = int(date[0:2])
  if 59 <= year <= 99:
      date = '19' + date
  else
      date = '20' + date

and then use strptime with the %Y directive instead of %y.

I'd use datetime and parse it out normally. Then I'd use datetime.datetime.replace on the object if it is past your ceiling date -- Adjusting it back 100 yrs.:

import datetime
dd = datetime.datetime.strptime(date,'%y%m%d')
if dd.year > 2005:
   dd = dd.replace(year=dd.year-100)