You've asked two distinct questions there.
The first one is 3/10.
The second on is 21/400...
*watch this space*
EDIT: My bad... 21/200 (based on two equal d20 irrespective of when they are rolled)
EDIT2: Bugger, didn't read the question properly: first one is 3/200
And further to first edit, if the d20 of the '1d20 + 14' side of the expression is rolled first, then the probability is 3/80 (based on absolute fulfilment of the condition that 1d20 + 14 < 1d20)