If we can reformulate your example as a conditional, i.e. along the lines of :
every time I've played with Federer, I've won
we can try to analyze it as a Counterfactual conditional, exploiting Davis Lewis's analysis :
The semantics of a conditional A → B are given by some function on the relative closeness of worlds where A is true and B is true, on the one hand, and worlds where A is true but B is not, on the other.
On Lewis's account, A → C is :
(a) vacuously true if and only if there are no worlds where A is true (for example, if A is logically or metaphysically impossible);
(b) non-vacuously true if and only if, among the worlds where A is true, some worlds where C is true are closer to the actual world than any world where C is not true;
or (c) false otherwise.
In your case, we have no logical or physical or metaphysical impossibility against your palying tennis with Federer; thus, case (a) must be excluded.
Thus, we can say that the actaul world is much closer to a world were you play against Federer and lose the game than a world where you play and win.
If so, case (c) applies, and we can conclude that it is false.