Five of Cups – Love and Relationship Outcome
The Five of Cups in a Tarot reading is a about suffering a serious loss but there maybe something on a material level that you keep. The water under the bridge means that the situation cannot be changed but it is no longer important .
In the reversed position it maybe that you receive news that someone from the past is going to return.
Five of Cups – As a Person, Outcome and Feelings
Family-matters, care to be taken of them, sorrow or pleasure, emotion, material difficulties; there may be some advantage and some loss at the same time. News is certain to arrive. Subject to influences from the surroundings and apt to react too quickly thereon. A. E. Thierens, 
Five of Cups
Pictorial Key to the Tarot – Rider-Waite-Smith
By A.E. Waite (1911), tarot card illustrations by Pamela Colman Smith (1911)
A dark, cloaked figure, looking sideways at three prone cups two others stand upright behind him; a bridge is in the background, leading to a small keep or holding.
Meanings Five of Cups in a Reading
It is a card of loss, but something remains over; three have been taken, but two are left; it is a card of inheritance, patrimony, transmission, but not corresponding to expectations; with some interpreters it is a card of marriage, but not without bitterness or frustration.
Five of Cups – Reversed
News, alliances, affinity, consanguinity, ancestry, return, false projects.
Additional Divinatory Meanings
Generally favourable; a happy marriage; also patrimony, legacies, gifts, success in enterprise.
Additional Meanings – Reversed
Return of some relative who has not been seen for long.
By S. L. MacGregor Mathers, c 1888
Five of Cups
Five of Cups – Union, Junction, Marriage, Inheritance.
Divinatory Meanings – Reversed
Arrival, Return, News, Surprise, False projects.
General Book of the Tarot
By A. E. Thierens, 
Five of Cups
Inheritance, legacy, succession, gift, testament, transmission, tradition; all of them “not corresponding to expectations; with some it is a card of marriage, but not without bitterness or frustration.” (Waite) Reversed: Family, forefathers, ancestry. Liaison, alliance, affinity, acquaintance, consanguinity. Race. “It is a card of loss.” (Waite)
The Water coming on the First house, the ascendant, and water having to do with the family, we may conclude, that family matters will come naturally to the querent in this case, just as they were swept from him or evaded by him in the preceeding one. Still we cannot see, that the card should denote the members of the family in particular, as mentioned by Papus and others. Now ‘family-matters’ may include inheritance as well as marriage, but so many other things may also be included that it is difficult to enumerate them, and none of them is indicated particularly. So we do not think it wise to say anything more definitely about this. The water of the feelings coming on the ascendant indicates sensitiveness and emotion, which may bring sorrow A or pleasure, but generally mixed experiences and not without care. There may be material losses in consequence.
The Oracle of the Tarot – Exoteric Tarot
By Paul Foster Case (1933)
Five of Cups
A serpent rises in the vesica over the cups. It is the ancient symbol of the sign Scorpio, to which this card specifically refers. Yet it is also the serpent-power which brings illumination; so there is a flame of light over its head.
First decanate of sign Scorpio, October 23rd to November 1st, ruled by Mars.
No meaning of this card is really good, but they are worse if ill-dignified. Loss in pleasure; vain regret; disappointment, sorrow and loss in those things which have been much desired; treachery, deceit; unexpected troubles and anxieties; disappointment in love, broken engagement, broken friendship.
More information on the Five of Cups Tarot card.