[1] https://mdao.grc.nasa.gov/publications/AIAA-2015-1587.pdf
[2] https://github.com/OpenMDAO-Plugins/Hyperloop
[3] http://www.popsci.com/hyped-up-startups-race-hyperloop-life
Only if the vehicles are self propelling from the ground, and if you refer back to trains really they are just pushing air in front of them, with some air escaping past them.
If there were not ventilation systems to allow the air behind the train to be filled, the train would need to work harder to essentially pull the air behind it.
At least, that's my understanding.
If the vehicles are not self propelling from the ground, and propel with air, like the original hyper-loop proposal, they are actually pushing air backwards to their direction of motion, which would stop any such forward moving air flow develop.