The whole answer for those who care is :

There are 2 ways that a horse can win 2 maidens. The first being a Maiden flat race and a Maiden Hurdle. The other way is for a horse to run 2nd in a maiden and then winning another maiden shortly after. The first maidens winner ends up posting a positive swab result and is disqualified thus the horse that ran second is now promoted to 1st. Thus it has won 2 maidens.

Nice work Imagele.