The [1-99] doesn't do what you think. It is a character class which will match a single digit in the range one to nine. That corresponds to what you see.

You can match and test with

while (<DATA>) {
    print if
        /^192\.168\.(\d{1,3})\.(\d{1,3})\b/
        and $1 > 0 and $1 < 100 and $2 < 256;
}
[download]