Graphs like these are based on a _complete cross-sectional area_. Myelination adds thickness, so if you want to add myelin outside and keep the same diameter, you have to have a smaller lumen inside the axon.
As you can see in the "unmyelinated" plot versus diameter, smaller fibers have lower conduction velocity. Since the benefits of cross-sectional area are most important at small diameters (because the velocity changes with the squart root of diameter), for small diameter axons you end up losing more from losing internal area than you gain from adding external insulation.
If you keep the internal diameter the same and just add myelin, you will always increase the conduction velocity, but the total diameter including the myelin won't be the same anymore.