I get a compilation error for _ssl when building on OSX 10.9 using the 10.9 SDK, the relevant error:

/Users/ronald/Projects/python/rw/default/Modules/_ssl.c:1029:24: error: no member named 'crldp' in 'struct x509_st'
    dps = certificate->crldp;
          ~~~~~~~~~~~  ^

Looking at /usr/include/openssl/x509.h in the 10.9 SDK that does not have a crldp member:

struct x509_st
        {
        X509_CINF *cert_info;
        X509_ALGOR *sig_alg;
        ASN1_BIT_STRING *signature;
        int valid;
        int references;
        char *name;
        CRYPTO_EX_DATA ex_data;
        /* These contain copies of various extension values */
        long ex_pathlen;
        long ex_pcpathlen;
        unsigned long ex_flags;
        unsigned long ex_kusage;
        unsigned long ex_xkusage;
        unsigned long ex_nscert;
        ASN1_OCTET_STRING *skid;
        struct AUTHORITY_KEYID_st *akid;
        X509_POLICY_CACHE *policy_cache;
#ifndef OPENSSL_NO_RFC3779
        STACK_OF(IPAddressFamily) *rfc3779_addr;
        struct ASIdentifiers_st *rfc3779_asid;
#endif
#ifndef OPENSSL_NO_SHA
        unsigned char sha1_hash[SHA_DIGEST_LENGTH];
#endif
        X509_CERT_AUX *aux;
        } /* X509 */;

Note that OSX ships a fairly ancient version of OpenSSL, libssl.dylib is 0.9.8. 

(Marked as a regression because 3.3 and 2.7 can be build with the system version of OpenSSL).