Easy, but you can't create **random** teleport. Create one object with trigger texture. click button to entity and create trigger\_teleport. And of course give that trigger\_teleport a name. Next what you need to do is to find in entities info\_teleportdestination and give it a name and place it where you want for player to teleport. Select your trigger\_teleport and you will see teleport destination option, there type the name of your info\_teleportdestination. And select trigger\_teleport go to outputs click add and: On Teleport, your trigger\_teleport, disable, and fire only once. And that's how you do it buddy. If you can't make it, I'll create it for you. :)
And don't forget to use filter\_activator\_team if you want only Ts or CTs to teleport.
Make a trigger\_once activate a point\_teleport. Then make the point\_teleport -> Teleport -> !pvsplayer.
Edit: This should make it teleport the nearest player, I'm almost certain of. If it doesn't work, you can make the point\_teleport -> Teleport -> !activator.
That means whoever walks into the trigger_once brush gets teleported to where the point\_teleport is.
Edit #2: If you want to perfect it even more to make it completely random, put a triggerbrush on each of the 32 player spawns which fires a servercommand to give all the players their own "targetname". Then through a logic_auto (OnMapSpawn or on round start) activate a logic_case (if I remember correctly) which have a case for each player to teleport them using a point_teleport. In theory this should work if I'm not forgetting something.