Writing something like Simplify[x<0,x<0] returns True because the second argument to Simplify is interpreted as an Assumption that is considered to be true.
Had the second argument been eg x==1, evaluating the preceding code segment would produce False; that result is not unexpected, since assuming that the value of x is equal to 1 (a positive number), the truth-value of x<0 is expected to be False.
Now, when Mathematica evaluates {x,y}<0, it returns the same expression (provided that there are no other rules related to symbols x and y). This
should not be surprising; it happens because Less[List[x,y],0] (which is the FullForm equivalent expression of {x,y}<0) is a valid Wolfram Language expression like eg x>0; evaluating x>0 also returns x>0 (again assuming no rules are attached to symbol x beforehand).
An expression like {x,y}<0 might anticipate an evaluation result like {x<0,y<0}, but such an expectation is not warranted. The function (or 'operator') Less does not thread over its arguments (as has already been pointed out by other answers) much as some numeric functions like eg Exp or Log do.
Evaluating Attributes[Exp] or Attributes[Log] should return a list of the attributes attached to each symbol; in the case of eg Log it returns {Listable, NumericFunction, Protected}; the presence of Listable in the Attributes list of Log 'allows' the user to expect that eg Log[{0,1}] will evaluate to {-Infinity, 0}.
The evaluation of {x,y}<0 does not return what's anticipated, because Less is not Listable.
What this means for the question at hand, is that when Simplify is presented with an Assumption that does not evaluate to a relevant relation (it simply reads Less[List[x,y],0]) for the expression it is expected to simplify-x<0 in this case-it returns the best result it can deliver ie x<0, which-in this case-is the same expression it was presented with, in the first place.
This result is equivalent to eg Simplify[x<0,y<0]; again, in this case, too, the Assumption does not assist in simplifying the expression passed as a first argument to Simplify.
{x, y} < 0to be nonsense. – Michael E2 Feb 06 '18 at 02:53Simplify[x < 0, Thread[{x, y} < 0]]– Bob Hanlon Feb 06 '18 at 04:06Listableinequalities are possible withPositive,Negative, etc.:Simplify[x < 0, Negative[{x, y}]]. – Michael E2 Feb 06 '18 at 12:39