Rupp, 99 times out of 100. Rupp knows how to race for place. Hall knew only how to run for time. The chances that he'd have a great day and simply run away from Rupp are slim.
Rupp is the sort who would rather win in 2:09 than be 5th in 2:05. Hall would rather be 5th in 2:05 than win in 2:09. The Rupp type wins races far more often.
Or Rupp would rather face 2:09 competition than 2:05 competition.
If Rupp is in that 2:05 race with Hall, who wins?