While it's theoretically possible, it's unlikely.

First, organisms evolve based on mutations and differential reproduction, so you would need the same sorts of mutations and the same sort of selection pressures. Both of these are unlikely, the conditions just are not the same. Also, why did D go extinct? Because they died out because of over competition in their niche, some parasite, etc. ; well, it would affect a new D too. And of course mutations are random, so it's pretty much impossible to exactly replay.

That said, we do have lots of examples of convergent evolution, where different organisms have evolved to fill in niches in different areas. See: https://en.wikipedia.org/wiki/List_of_examples_of_convergent_evolution . Let's say there is a land that doesn't have a large diversity of birds (say, the Galapagos). The first birds that arrive will radiate (diversify through evolution) to fill lots of different niches, such as eating nuts, eating fruits, eating insects, even though they had the same progenitor species. Interestingly, the evolved organisms filling the niche don't do it quite the same way, because evolution adapts what is at hand.