Between the converters themselves? Probably not. Just about any converter these days has gone way beyond the limits of audibility. However between the implementation? Possibly. There's a lot of room to do a suboptimal implementation of all the stuff surrounding a DAC. Remember that the DAC chip itself is only one of a number of components needed to get the signal up to line level. Also there can be issues with matching the output to the device you are feeding, and problems getting introduced that way. For example if a DAC has too low a signal, maybe you have to drive the preamps on your monitors harder than they like, and they introduce noise because of it. Or the signal is too hot and you have to attenuate it, but the attenuator has non-linearities at low settings (they often do) and you get a channel imbalance for it.
Those are just simple examples, there is plenty else that could potentially happen.
So what you are getting with a good expensive, properly designed, DAC like a Benchmark 2 is basically insurance/peace of mind. You know that they did a really good job on the design and implementation, can check the measurements to back that up, and it has the flexibility to be adjusted as needed for whatever it is feeding. You eliminate it as a potential source of issues.
In many cases, it won't be audibly different. It certainly isn't something I'd prioritize spending money on (I don't have one), but if you have a really good setup, I can see the appeal to make sure that it isn't an issue.
If you do want something like that though, make sure to get one that is verifiably well designed, meaning they have taken, and are willing to show you, the measurements. If a company says it was "designed by ear" and is light on technical details, go elsewhere. We can measure WAY more accurate than we can hear, and we can use measurements to spot problems that only appear in edge cases. I'm a fan of Benchmark for that reason, they provide you with a ton of detail (and you can get more if you ask).
Finally you can always try the gold scientific standard of the blind test if you can get a place that'll do a money-back in studio test on the DAC and get a friend to help you. See if you can reliably hear a difference when you don't know which is which. If you can't, then send the DAC back :).