I 'm looking for an antonym that has all the subtleties that serendipity carries in it.

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    quite a good question. As I understand you want to express a lack of fortune but not necessarily a bad fortune/ misfortune? Jan 23 '15 at 8:33
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    @AverageGatsby An unfortunate discovery, coincidence, or happenstance - something along those lines.
    – user15851
    Jan 23 '15 at 8:43
  • Somewhere on the other side of the Venn circle would be accident-prone. Jan 23 '15 at 10:00
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    "Bad luck" is an obvious choice. Or one might consider some of the antonyms of "Midas" touch. "Can't catch (or, sometimes, buy) a break" is one possibility. Urban Dictionary has the "Sidam touch".
    – Hot Licks
    Jan 23 '15 at 13:19

I think “vicissitude” comes close. The definition of vicissitude according to Oxford Dictionaries is: “(usually vicissitudes) A change of circumstances or fortune, typically one that is unwelcome or unpleasant”

Example sentences: 1. Governments cannot protect citizens from all the circumstances and vicissitudes of life.

  1. Perhaps nothing can demonstrate the city's vicissitudes better than the changes of its landmarks.
  2. Losing your job is just one of the vicissitudes of life

If you think of serendipity in a broader sense of: "all the variables in the universe coming together perfectly, like pieces in a jig saw puzzle," then "chaos" is a good antonym.

If you want to refer to a single instance, then "ill-fated" may fit.

  • Infelicity. Depending on what you mean by sublety. I just like the sound of it, which harmonizes (and rhymes) with serendipity. Jan 25 '15 at 0:39

While not a term for the condition, there is a term for the condition sufferer - schlimazel (also spelled schlemazel)

A consistently unlucky or accident-prone person. Oxford Dictionaries Online

The term is a Yiddishism adopted into English. Etymonline offers the following derivation

"born loser," 1948, from Yiddish shlim mazel "rotten luck," from Middle High German slim "crooked" + Hebrew mazzal "luck." British slang shemozzle "an unhappy plight" (1889) is probably from the same source. A shlemiel is the fellow who climbs to the top of a ladder with a bucket of paint and then drops it. A shimazl is the fellow on whose head the bucket falls. [Rep. Stephen J. Solarz (D.-N.Y.), 1986]

As noted, there is a related British term, shemozzle

A state of chaos and confusion; a muddle. Oxford Dictionaries Online