Rolling can make grass tiller which in theory should produce more grass. However heavy rolling can knock grasses growth back for a week or so. Having said that some farmers roll regardless as it looks good and their farther used to do it.aking the world better, one answer at a time. A farmer should only really roll a field no later than March as the ground gets too hard in april to flatten out, also you won't destroy any ground nesting birds nests in March.