In my CZ SP-01, which probably has the shortest freebore of any common 9mm gun around, I load Berry 115gr FP to 1.045" with 4.2gr of Win231. These shoot really well, so much so I used them in IPSC competition. (I believe this load and length is listed in Hornady's 4th or 5th.)
If you are worried about case volume, then it's a simple thing to measure the Winchester round, then measure the naked Winchester bullet length. With some 3rd grade math you can then calculate the "height" of the bullet's base at that OAL. Then, using the Berry's FP bullet length, you can easily arrive at a OAL than will result in the Berry FP sitting at the same depth in the 9x19 case. If nothing else, you may not wish to go any deeper (lower) on your OAL than this number.
However, that is not the full story by a long shot. The FP's shoot great, but due to the feed ramp angle, every gun has an optimal OAL for these to feed well too. So like most shooters, you probably want the bullet to shoot well AND feed well. If you load 10 of each (1.045, 1.055, 1.065, etc), you'll find a sweet spot. Just be careful NOT to run the bullet into the rifling, or out of the case mouth.
Hope this helps!