Five of Swords – Love and Relationship Outcome
The Five of Swords in a Tarot reading indicates going through an extremely difficult period and feelings of being wronged that is holding the relationship back and creating financial difficulties. However, all is not necessarily lost and things may work out.
In the reversed position it means the same.
Five of Swords – As a Person, Outcome and Feelings
Affliction, crisis, morose disposition, bitterness, impotence, lack of self-respect, or self-confidence; it may be that self-confidence is ascertained by some struggle or conflict; difficulties, which after all may prove very useful but necessitate much self-discipline. In the same way discipline of children is necessary. Enterprise or expansion is impossible or not advisable. Things indicated by this card may indeed be bad-looking or unpromising. There will be a question of a loss in most cases. A. E. Thierens, 
Five of Swords
Pictorial Key to the Tarot – Rider-Waite-Smith
By A.E. Waite (1911), tarot card illustrations by Pamela Colman Smith (1911)
A disdainful man looks after two retreating and dejected figures. Their swords lie upon the ground. He carries two others on his left shoulder, and a third sword is in his right hand, point to earth. He is the master in possession of the field.
Meanings Five of Swords in a Reading
Degradation, destruction, revocation, infamy, dishonour, loss, with the variants and analogues of these.
Five of Swords – Reversed
The same; burial and obsequies.
Additional Divinatory Meanings
An attack on the fortune of the Querent.
Additional Meanings – Reversed
A sign of sorrow and mourning.
By S. L. MacGregor Mathers, c 1888
Five of Swords
Five of Swords – Mourning, Sadness, Affliction.
Divinatory Meanings – Reversed
Losses Trouble (same signification, whether reversed or not).
General Book of the Tarot
By A. E. Thierens, 
Five of Swords
Loss, dishonour, degradation, defeat, ruin, reversal of fortune, diminution, wronging, bad luck, destruction, etc. Reversed: Much the same, burial, obsequies. It is also said to represent a thief and theft, corruption, seduction, plague, and all that is hideous and horrible.
The element of Earth with its influence of Mars and Saturn on the Fifth house, ruling the heart, cannot be very ‘favourable’ in the ordinary sense of the word and is certain to lead to a feeling of being wronged by the world, an inner bitterness and impotence, which hinders enterprise and business; so these will suffer. And the heart itself, being of precisely the opposite nature, will suffer and find things awkward, horrible, hideous, etc. In the same way this card must indicate affliction of honour, which is ruled by the Sun. Moreover, as “from the heart are the issues of life,” the card may indicate vice and a bad use of the inner or spiritual forces. Still there is another possibility, and this is given by Mr. Waite when he says that this card’s image signifies a man who “is master of the field.” So he may be if the inner force is great enough to conquer the afflictions which assail him. In other words, it need not be a card of absolute defeat, for there may very well be a good result, but nevertheless it denotes serious difficulty and a critical moment or period in life, in which the querent or some one to whom it relates will be threatened with the above-mentioned sad effects.
The Oracle of the Tarot – Exoteric Tarot
By Paul Foster Case (1933)
Five of Swords
The scourge combined with the ankh is a symbol of suffering, of the slings and arrows of outrageous fortune. Yet the pains and sufferings bring understanding, and are the result of the Querant’s own Karma. The suffering is not really unjust.
The first decanate of Aquarius, under the rulership of Saturn and Uranus, from January 20th to January 29th.
Decision adverse to Querant in any matter of material nature; but in spiritual questions the end of a course of action in apparent defeat which will nevertheless produce a good ultimate result. In any case a card of failure, defeat, trouble, poverty, and anxiety. The Querant is probably the subject of more or less slander.
The troubles are intensified, and are probably more definitely the result of the Querant’s own failings; particularly, in this instance, does the Five of Swords suggest loss through the Querant’s own avarice.
More information on the Five of Swords Tarot card.