Single-elimination tournament with 2n players,
random pairings each round, and the better player always wins.
Tournament size
16 players
Choose n so total players = 2n
P = 2n-1 / (2n - 1)
Half containing player #1
If player #2 is placed anywhere in this half, then #1 and #2 must meet before the final.
Opposite half
If player #2 is placed anywhere in this half, then #1 and #2 can only meet in the final.
Probability that #1 and #2 meet only in the final
8 / 15
53.33%
Round-by-round view
Since player #1 beats everyone, #1 always reaches the final.
Player #2 loses only to #1, so #2 also reaches the final
iff #2 avoids #1 in every earlier round.
That happens exactly when #2 starts in the opposite half of the tournament tree.