The disclosed computer-implemented method may include (i) receiving a first transport request and a second transport request, (ii) evaluating a fitness of matching the first and second transport requests to be fulfilled by a transport provider, based at least partly on a transportation overlap between the first and second transport requests, (iii) generating a simulated future transport request, (iv) evaluating a fitness of matching the first transport request with the simulated future transport request, based at least in part on a transportation overlap between the first transport request and the simulated future transport request, and (v) matching the first and second transport requests based at least in part on the fitness of matching the first and second transport requests and based at least in part on the fitness of matching the first transport request with the simulated future transport request. Various other methods, systems, and computer-readable media are disclosed.