The exact solution depends on the challenger's and "1"'s respective win rates. However if we assume both have a 50% cover rate and no pushes on any game, the contest win rate with no shared picks is 31.4% (challenger wins with 5-0 no matter what EOG does, "1" takes the case of a tied record and the challenger must have winning record).
OTOH, if all picks are shared, the win rate is 1/32 or 3.1%, With 1 shared pick, the contest win rate is 29.1%; with 2 shared picks, 26.6% win rate; 3 and 4 shared pick win rates are 23.44% and 18.8% respectively.
90% over the last two weeks and nothing to show for it in the free contests. You know betting is getting hard when 90% doesn't get you anything in a free roll. Oh wait I have that bulge in my pocket....wonder what that is.