First, let’s take a look at the race conditions as they appear in Equibase.
The first thing they says is, “Starter Optional Claiming $50,000”.
Sometimes you will see a similar condition that says, “Allowance Optional Claiming $xx,xxx”.
As an example, here are the conditions for the 8th race at PRX on 1.15.13.

In one case it is called a “Starter” and the other an “Allowance”. They both go on to say “Optional Claiming” with a specified claiming price, whatever it may be.
So, the idea is this. You can enter your horse to be claimed for the specified price
OR NOT.
With that in mind, let’s go over the condition in question.
The condition is in two parts. It starts by saying...
1 - “For Fillies three years old which have started for a claiming price of $50,000 or less
AND which have never won a race other than maiden or claiming,
OR
2 – claiming price $50,000.
Here is the Equibase condition.
Therefore, in the case of the #1 horse, has this horse been entered to be claimed for $50,000?
A little research reveals that in its' last race it was entered to be claimed. Here is the chart.
If so, that it how it is eligible to run in this race, even with the 2 wins, just like it was in its' last race.