If a booster wins three and loses two, you have been delivered one win and that is what the order counts. Some sellers count games won and let the losses quietly cancel out what you paid for; this page is priced on the net figure and the orders are tracked on it. It is the single most important sentence on this page.
When you are close. A handful of net wins moves you through a promo or off the edge of a demotion without committing to a full climb, and it costs a fraction of one. If the target is several divisions away a climb is cheaper per LP, and we will say so rather than sell you twenty wins.