You can do it with:
https://forums.alliedmods.net/showthread.php?p=2105028
Edit: Here's an example config for the random filter.
Code:
"SuperTargeting"
{
"@random"
{
"text" "a random person"
"alive" "1"
"random" "1"
}
"@randomred"
{
"text" "a random Red person"
"alive" "1"
"random" "1"
"team" "2"
}
"@randomblue"
{
"text" "a random Blue person"
"alive" "1"
"random" "1"
"team" "3"
}
}
The "random" "X" can be changed (X) to what ever amount of players you want to select randomly, this also follows any other targeting filters so you can customize to select a random scout on the red team that is currently alive. (just for an example).