I managed to compile ssldump 0.9b3 against openssl1.0.0 with a few tweaks (the config.guess for host and ssldecode.c for the missing md5 header). The executable ran and managed to capture some ssl packets when built without linking against openssl however, the executable refuses to run with "ERROR: Couldn't create network handler" when compiled against the openssl library.
I use fink to manage the dependencies, and am running on a Mac OS X 10.8.
terminal output from configure to run
Terminal output is attached, please don't hesitate to ask me if you need more information