Hitting through mid wicket requires you to time the shot early. Unfortunately, DBC 14 doesn't really support true 360 degree shot placement, i.e. you can't play the shots to each part of the ground in the 360 degree arc as you can in real life or you could in Ashes cricket 2009. You just have a few pre-determined areas you can place your shot in DBC 14. E.g., if you play a cover drive the well timed shot goes through extra cover and if you have an extra cover fielder in place, no point in playing the shot. If you time the shot a bit early or a tad late the shot follows a slightly different arc but the shot is not a well timed one.
Same is the case with playing through mid wicket. A well timed clip goes through the Square Leg or Forward Square leg region but if you time the shot early or play an early pull shot, the ball will go through the mid wkt region but it won't be well timed and will rarely reach the boundary. Hopefully this will be addressed in DBC 17 and we will have true 360 degree shot placement and we should be able to play well timed shots anywhere based on the direction Right Stick is pointing.