Answer
No, both will have same amount
Work Step by Step
Let us assume the capacity of small glass is X ml. So after pouring wine, the large glass will have X ml of wine. Now let us say we poured Y ml of water in the large glass. The first observation we make is $Y\leq X$, because we are pouring some water from small glass so it can be at max the capacity of small glass that is X.
So now there will be X ml wine and Y ml water in the large glass. Now we will refill the smaller glass with Y ml content of large glass. Since the wine and water is mixed in large glass the wine sent into the small glass will be-
$\frac{X}{X+Y}\times Y$
The water sent in the small glass will be-
$Y - $ wine sent in small glass
=> $Y- \frac{X}{X+Y}\times Y$
The water left in the large glass will be-
$Y-$ water sent in the small glass
=> $Y - (Y- \frac{X}{X+Y}\times Y)$
= $\frac{X}{X+Y}\times Y$
This is the same as the amount of wine in the small glass.
The trick is defining variables and tracking the amounts of wine and water explicitly, instead of trying to reason qualitatively.
