With this config:
Listen *:424 https
<VirtualHost *:424>
ServerName A
SSLCertificateFile 1.crt
</VirtualHost>
Listen *:444 https
<VirtualHost *:444>
ServerName A
SSLCertificateFile 2.crt
</VirtualHost>
connecting to either 424 or 444, I get cert 1.
With this config:
Listen *:424 https
<VirtualHost *:424>
ServerName A
SSLCertificateFile 1.crt
</VirtualHost>
Listen *:444 https
<VirtualHost *:444>
ServerName B
SSLCertificateFile 2.crt
</VirtualHost>
connecting to 424 gets me cert 1, and connecting to 444 gets me cert 2.