Fives are all about loss and learning and change. The card suggests a hard loss that carries with it a lesson and an important change. The idea of the fives seems to be that loss is important if things are going to push past the status quo to something new, different or better. Because of this, the reversed meaning does not, necessarily, turn loss into gain....
Five of Swords Reversed
This is a card all about losing a fight, in particular a battle of wits or communication. There is a suggestion that the other side might have cheated or used underhanded methods. Reverse this and the card does not really say that the querent will win the argument instead. A blocked interpretation seems most apt here, and that interpretation suggests that the argument drags on. If losing the argument is the energy, then blocking it means that there is no loss...but no win either. Just an on-going battle.
Another possibility is that the querent does win the argument - but does not feel that they've won. It is a hollow win. And yet another interpretation (upside-down), suggests that neither side wins. All the swords are lost, everyone loses.
Five of Wands Reversed
In this card, the querent is warned that he will lose his individuality. That he will be struggling to stand out among others equally talented. What's positive about this card is that there is a struggle, a belief that one can stand out. Thus, reversed, this card suggests that the person has no faith in winning such a struggle, and so doesn't even try.
This is the card of the person who walks in for a job interview, sees all these other talented people waiting, and walks out. They say, "What's the use of even trying. I can't possibly compete with them!"
Five of Cups Reversed
Upright, this is a card about regret for lost love or other good feelings or people. What is always pointed out about his card is that even though the man weeps over the spilled cups, there are two standing that he's not seeing. Not all that is good is gone.
One can well imagine how dark, therefore, is the reversed card. Turn it upside-down and the liquid in the remaining two cups is lost as well. Our weeping man has lost it all. Some because he spilled it himself, the rest because he didn't notice it and it evaporated. This is the stereotypical scenario of the man who weeps over the loss of a beautiful girlfriend, never seeing the plain girl who still loves him and is still there waiting for him. In the reversed card, the plain girl finally gives up and goes off in search of love elsewhere.
Five of Pentacles Reversed
The upright card suggests financial loss or a loss of luck/health. But there is still friendship. The material may be gone, but the spiritual is still there. Reverse it and our Church window is upside-down, suggesting that even institutions that would normally help the poor (charities, for example) are not there. Our poor folk are on their own.
Curious about this card when upright? Go to our Tarot Card Meanings.