After much tinkering I can now compile RTMPdump with PolarSSL 1.0.0
http://svnpenn.blogspot.com/2011/06/rtmpdump-mingw.html
Install required packages
mingw-get install libz
mingw-get install msys-wget
Install PolarSSL
wget http://polarssl.org/code/releases/polarssl-1.0.0-gpl.tgz
tar xf polarssl-1.0.0-gpl.tgz
cd polarssl-1.0.0
make CC=gcc APPS=
make DESTDIR=/mingw install
Install RTMPdump
wget http://repo.or.cz/w/rtmpdump.git/snapshot/6230845.tar.gz
tar xf 6230845.tar.gz
cd rtmpdump
make SHARED= SYS=mingw CRYPTO=POLARSSL LIBZ='-lz -static' VERSION='2.4\ git-6230845\ 2011-9-25'