Five of Cups reveals that in the Applicant's case there is a good chance that some fortunate circumstances could arise. This means that, despite possible difficulties, the Applicant still has a good chance of being able to do something positive and profitable. The card also shows that the Applicant must stay focused on their goals in order to successfully achieve them.
The High Priestess reversed shows that within the Requester, the Adversary could be an obstacle or difficulty to overcome. However, the card shows that the situation is not as negative as it may seem at the beginning: in fact, although there may be difficulties or obstacles to face, there are also opportunities and possible advantages to be drawn.
In conclusion, the cards suggest that while there may be problems to deal with, the Applicant may have a good chance of being able to win something in the lottery. The answer to the question is therefore "Yes", and it is highly probable that the Applicant will be lucky enough to win a sum of money.