sub is_match { my $term = shift; my $inner = ($term =~ m/^A(.*)Z$/)[0]; return undef if (!defined($inner)); return undef if $inner eq ""; return $inner if $inner =~ m/^\s+\S/; return undef; } prints:..... AZ: RESULT=NO MATCH AZZ: RESULT=NO MATCH A SOMETHING Z: RESULT=" SOMETHING " ASOMETHINGZ: RESULT=NO MATCH A Z: RESULT=NO MATCH A ZZ: RESULT=" Z" AAZZ: RESULT=NO MATCH AA ZZ: RESULT=NO MATCH ZA: RESULT=NO MATCH