The classic notion of a win–win situation has a key flaw in that it cannot always offer the parties equal amounts of winningsbecause each party believes they are winners. In reality, one party may win more than the other. This strategy is not limited to a single product or negotiation; it may be applied to a variety of situations in life. We present a novel way to measure the win–win situation in this paper. The proposed method employs fuzzy logic to create a mathematical model that aids negotiators in quantifying their winning percentages. The model is put to the test on real-life negotiation scenarios such as the Iraqi–Jordanian oil deal and iron ore negotiation (2005–2009), in addition to scenarios from the game of chess. The presented model has proven to be a useful tool in practice and can be easily generalized to be utilized in other domains as well.