The Strength card symbolizes courage in the face of something that looks bigger and stronger than us. It's the inner power that conquers fear, it's self-discipline and perseverance. The Five of Cups is the card of loss, regrets and disappointments. Often it appears when we go to war with life, when we refuse to accept that things sometimes don't go the way we want them to go. The Strength and the Five of Cups combination is about facing adversity with grace and courage.
The elements of the cards are Fire (Strength) and Water (Five of Cups). Fire and Water do not support each other, on the contrary, they fight each other. So we should expect that the energies of the cards will be in contrast. The Strength wants to put emotions (Five of Cups) under control, but the Water in Five of Cups won't give up without a fight. So we may experience mood swings and loss of direction when this combination appears. However, in all likelihood, the Strength -being a major arcana card- will dominate eventually and things will stabilize.