In the first case, there are only two balls. In the first two rounds, Andrew must have drawn the 2 and Jerry must have drawn the 1, and vice versa in the final round. Thus, Andrew's sum is 5 and Jerry's sum is 4, so Jerry never has a higher total.
In the second case, each game could've had three outcomes — 10 - 2, 10 - 1, or 2 - 1. Jerry has a higher total if and only if Andrew won 2 - 1 in both of the first two rounds, and Jerry drew the 10 in the last round. This has probability .