Special Kentucky Oaks and Derby Trivia Challenge

It's time once again for the special Kentucky Oaks/Derby trivia challenge, which comes in ten parts. Your challenge: Answer all ten questions before the Kentucky Derby's post time on Saturday,

1) Which Kentucky Oaks winner's victory was part of a 1-2 finish in the race for her breeder, her owner and her sire?

2) Pretty is as pretty does---this mare won a broodmare class at a horse show and also produced a Kentucky Oaks winner. Who was she, and who was her Oaks-winning daughter?

3) What woman trained both Kentucky Oaks and Kentucky Derby starters in the same year, and how did she fare with her entries?

4) This Kentucky Oaks winner may well have been the first such winner insured through Lloyd's of London. Who was she, and in what year did she score the win that led to her owner having her insured?

5) Which Kentucky Oaks winner broke her maiden against older males?

6) Which Kentucky Derby renewal led to the event known as the "Great Runout"?

7) Who was the first female jockey to compete in the Kentucky Derby, and where did she finish?

8) Which Kentucky Derby was the last to go off without a starting gate?

9) What horse was the lowest-earning Kentucky Derby winner of all time?

10) Which Kentucky Derby winner had the barn name of "Boyfriend"?