perl -ne "chomp; my ($ip) = (split q| |,$_)[2]; my $num; if ($ip=~m/\
.(\d+)$/){$num=$1} print qq|$ip\t$num| . `date ` if($num >= 1 && $num 
+<= 2);" fakesquidlog.txt

Prints
========
192.168.1.1     1Fri Apr 29 09:34:49 Central Daylight Time 2011
192.168.1.2     2Fri Apr 29 09:34:49 Central Daylight Time 2011
(Date format explain: I'm on Windows)
[download]

Fake squid log contains:
134135 22 192.168.1.1 XX 200 HTTP foobar.com johnny huh? JUNK
134136 24 192.168.1.2 XX 200 HTTP foobar.com johnny huh? JUNK2
134137 25 192.168.1.3 XX 200 HTTP foobar.com johnny huh? JUNK3
[download]

You can easily change the line to append to a file using the $ip with  >>.

There is little sense in writing a large program for something that should be done as a one-liner.