It should, assuming you are not pulling a big wagon load of bales too. Can you let them drop on the field and pick thm up in a seperate operation? Or let the customer pick them up directly, if selling. Nicer shaped bales if they drop, compared to having gone thru a thrower. Also, if the 375 has a thrower, it takes power. Disconnect it.
It might.....the small 5X4 bales don't usually take as much HP, but I think you'd be pushing that little tractor pretty much to the max. You'll likely have to make smaller bales. 40 hp is the minimum for a Vermeer 5410 and it will give a 40hp tractor a good workout.