It's not at all uncommon to gear up to ovulation and not succeed. You can see all the signs of impending O like EW CF and OPK+'s and then something delays O. Many common things can cause this delay like stress, illness, injury, diet changes, strenuous exercise, etc. but the most likely cause of this is simply your returning fertility. It often takes several attempts to finally O for the first time postpartum, especially while breastfeeding. And to answer your title question, yes, you will likely O prior to your first pp bleed... 2/3 of women do. But only about half of these women will have an adequate luteal phase to sustain a pregnancy (so 1/3 of women total).... two things to keep in mind.
Since you are getting HPT- at 14 DPO it is most likely that you did not actually ovulate when you think you did or have not yet even ovulated at all. You could get hormonal bleeding at some point down the road, but more likely you will see (or have already seen?) another patch of EW CF and your body will try to O again. This is where temping is very helpful. Only temping can confirm O so that you know that pregnancy is possible or that AF is really on its way. Have you tried temping before? If not and it interests you, just post for more details on how to get going. Good luck!