I have a version of Lynx 2.8.8.14 with SSL enabled which I successfully configured and compiled in Cygwin on July 20, 2012. I have confirmed that the compile now fails as reported, both with ssl 1.0.1e-2 and 1.0.1c-2, the only previous version which cygwin currently allows me to install. So, perhaps there was an earlier version extant in July which permitted a successful compile. I can send you the exe file (or config log or anything else) if you think that might help reveal what release was in use.
Not that all is well with the successfully compiled version. Whenever I access a site with https now, I get a prompt: "SSL error: unable to get local issuer certificate - Continue?" This definitely did not happen in July when I built the image, but I cannot tell you when it did start. This also happens when I use the suggested
workaround (define CRYPT etc.) with the current release.
Finally, I noticed during this investigation that, if I try to build on Cygwin with ssl and don't have ssl installed on my system, configure and make nevertheless complete successfully (without ssl of course). I don't know if this is intended, but it seems wrong.