The answer to question 1 with 1 min 51 sec (that is, $n=111$ seconds) is yes. The answer to question 2 with 1 min 57 sec (that is, $n=117$ seconds) is no. Both answers are special cases of my solution that fully settles this puzzle for all possible numbers $n$ of seconds!
Question: Was there necessarily a moment in the game, when the clock of one player showed exactly $n$ seconds less than the clock of the other player?
Since 2 hours 30 minutes are exactly 9000 seconds, one would expect that the answer changes at 9000/80 = 112.5 seconds. But surprise, surprise, this is not correct!!
If $n\le114$ then the answer is yes.
If $n\ge115$ then the answer is no.
For $n\le114$, assume that the time difference never is $n$. Then the first move of first player takes at most 113 seconds as the second clock shows 0. Then the first move of the second player takes at most 113 seconds more than the time on the first player's watch. Then the second move of the first player takes at most 113 seconds more than the time on the second player's watch. Continuing this way we get by mathematical induction:
After move $m$ of the first player, his watch has traversed at most $113*(2m-1)$ seconds.
After move $m$ of the second player, his watch has traversed at most $113*(2m)$ seconds.
After move 40 of the first player, his watch has traversed at most $113*(2*40-1)$ = 8927 seconds. This is below 2.5 hours. There is a contradiction.
For $n\ge115$ construct a game where the first move of the first player takes 114 seconds. The first move of second player and all moves 2,...,39 of both players take 228 seconds.
After the first move of first player, the difference has gone up from 0 to 114. The first move of second player brings the differences down from 114 to -114. The next move of the first player brings the difference up to 114 again. The next move of the second player brings the difference down to -114 again, and so on.
After move 39 of the second player the difference is down at -114 again.
The watch of the first player has traversed 114+38*228 seconds, this is 8778 seconds. The watch of the second player has traversed 39*228 seconds, this is 8892 seconds. Move 40 of the first player takes 222 seconds and brings the difference up to +108. Move 40 of the second player takes 108 seconds and brings the differences down to 0.
The difference always stays between -114 and +114 and the watches are never $n\ge115$ seconds away from each other.