Given
A horse race 10 entries
One person owns 5 of these horses
Procedure
There are
N=10C5 ways of randomly choosing 5 horses out of 10.
where
N=10!/(5!5!)=252
We assume that
1. order does not count,
2. winning probabilities are equal among horses,
3. results are completely random.
Then the owner has one chance in 252 that his 5 horses are placed 1st to 5th.
1/252 = 0.0039