A race to two? Really? So what happens if you alternate the breaks, and Guy 1 breaks and runs, then Guy 2, breaks, comes up dry, and Guy 1 runs a second rack. Guy 2 only made one stroke, on a shot that has a lot to do with luck.
Do you make a ball, and do you have a shot at something?
And this is to settle a long league season?
Make the race to 5 or 7 or something. Round robin format. Take total games won into consideration. That way, even if everyone comes up with 1 match won, and 1 match lost, you'll still be able to go by who won the most games over all.