GrandFather already identified the problem in your code; in case you'd like to extend your program to other numerals (1,2,3 - as noted by gangabass), there's another variant:
use strict;
use warnings;
my $dates = '5th April - 12th April xxxx,
ssss, 3rd May - 23th May zzz!
1st June-2nd June, ddd';
my $subexp = qr{
(?:-\s*)? # may be we hit the second term
\d+ (?:st|nd|rd|th) # the day
\s+\w+\s* # the month
}x;
my @hits = $dates =~ /$subexp $subexp/xg;
print join "\n", @hits;
Regards
mwa
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