I see both Urahara and Ukitake being smarter than Isshin or Kyoraku. So, if these two make a good tactic and battle be finish before Ukitake's sickness got effect, team one can win.
If btw, Ukirake sickness take effect during fight, team two wins.
On the other hand, if we take away Ukitake's sickness and estimate how strong he would be while healthy, then I see team one winning again.
Because of many possibilities that need to be taken in consideration. I'm going with team 2 6/10 times.