Ok well SS and Hal would be a good fight but you have to remember SS was paired up against a very inexperienced and never trained Kyle Rayner right before the Amalgam series. Everyone was supposedly matched up based on power. Hal is the most powerful GL ever. He has done things with a power ring that no other GL has ever been able to do.
The GL ring would protect him from getting mind raped or whatever you all call it by all of the telepaths. I think he would make it to Tyrant or Odin and then he would lose.