When I compile and link against a local build of OpenSSL 1.0.0 (vanilla), I get the following errors in test_ssl:

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ERROR: testProtocolSSL2 (test.test_ssl.ThreadedTests)
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Traceback (most recent call last):
  File "/home/antoine/cpython/newssl/Lib/test/test_ssl.py", line 869, in testProtocolSSL2
    tryProtocolCombo(ssl.PROTOCOL_SSLv2, ssl.PROTOCOL_SSLv23, True)
  File "/home/antoine/cpython/newssl/Lib/test/test_ssl.py", line 736, in tryProtocolCombo
    CERTFILE, CERTFILE, client_protocol, chatty=False)
  File "/home/antoine/cpython/newssl/Lib/test/test_ssl.py", line 688, in serverParamsTest
    raise test_support.TestFailed("Unexpected exception:  " + str(x))
TestFailed: Unexpected exception:  [Errno 104] Connection reset by peer

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ERROR: testProtocolSSL3 (test.test_ssl.ThreadedTests)
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Traceback (most recent call last):
  File "/home/antoine/cpython/newssl/Lib/test/test_ssl.py", line 903, in testProtocolSSL3
    tryProtocolCombo(ssl.PROTOCOL_SSLv3, ssl.PROTOCOL_SSLv23, False)
  File "/home/antoine/cpython/newssl/Lib/test/test_ssl.py", line 745, in tryProtocolCombo
    ssl.get_protocol_name(server_protocol)))
TestFailed: Client protocol SSLv23 succeeded with server protocol SSLv3!

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ERROR: testProtocolTLS1 (test.test_ssl.ThreadedTests)
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Traceback (most recent call last):
  File "/home/antoine/cpython/newssl/Lib/test/test_ssl.py", line 914, in testProtocolTLS1
    tryProtocolCombo(ssl.PROTOCOL_TLSv1, ssl.PROTOCOL_SSLv23, False)
  File "/home/antoine/cpython/newssl/Lib/test/test_ssl.py", line 745, in tryProtocolCombo
    ssl.get_protocol_name(server_protocol)))
TestFailed: Client protocol SSLv23 succeeded with server protocol TLSv1!