Anyone good with statistics?

So me and a few friends played a couple of good ones. On our second game two players clicked up to fuedal at exactly the same second. Now, I understand that this is not uncommon for higher standard games, where early game is pretty "simliar" for all players. But for us, when clicking up can wary between 10.0 min and 15.0 min, it's a slimmer chance.

So what are the odds actually?

If asumed; four players

play 100 games

clicks up warying between 10.0 min and 15.0 min (300 possibilites)

assumed that each possibility has the same odds. What are the odds that 2 players click up at the same second atleast once?