We don't have a 99 model year catalog but I don't believe there is a dedicated drain for the anchor hold. That stated, you are correct in that what amount of water that is present after hauling in the anchor is designed to flow into the forward bilge. From there the water is designed to flow under the forward bulkhead, passing under the fuel tank platform where it passes through the rear bulkhead into the rear bilge.
Assuming all passageways are clear, water could theoretically flow from the stern to the anchor hold. That would require the stern to be higher than the bow and in that situation, you have more concerns than wet rode.
Water in the front bilge of these hulls is very common (hence a forward bilge pump). That is or can be caused by several things. First, by design, the forward bow section is "plumb". That design is to create more cabin headroom. That is arguable but it makes for great marketing. Still, water will collect in this section of the hull. Second, the conveyance bow to stern, through the hull may be compromised by trash that has found its way into the bilge. Members often check the bulkhead passages with a "snake" or water pressure. You may have a leaking thru hull for the forward bilge. And lastly, you would be surprised at how much water finds it's way into that forward bilge while underway from the rub rail connections and the bow rail mounting points.
With all that said, if you wish to keep water to a minimum in the anchor hold, you need to first seal it off from the forward bilge. You can accomplish this by accessing the small anchor compartment bulkhead via the front access cover in the cabin.
You may know all of the above already but that's the way the EXs (and Ospreys) are built.
Good luck.
