He says he would beat you. You say the strokes are wrong. One round settles nothing, because one round is mostly luck wearing a scorecard. So this plays the match ten thousand times and reports what actually happens — including the number of strokes that would make it an honest game, which is almost never the number you have been arguing about. Runs entirely in your browser. Nothing uploaded, nothing tracked.
Enter both handicaps and this free match simulator runs 10,000 matches to give you a real win probability and the exact stroke allocation that makes the game a coin flip.
The Grudge Match is a free online golf match simulator that answers the argument on the first tee with arithmetic instead of volume. Most groups hand over the full difference between two handicaps because that is what everybody does, not because anybody checked. In matchplay that default quietly favours the higher handicapper, because their disaster hole costs them one hole and nothing more, while yours costs you strokes you never get back. This tool simulates every hole of every match, so if you want to calculate fair golf strokes now, it takes about fifteen seconds and no signup.
No, and it is not close to always. Over one 18-hole match a two-shot gap is roughly a 60/40 proposition, not a formality. Golf has enough variance in it that a single result tells you almost nothing about who is better — which is precisely why the loser always wants to go again, and why he is statistically entitled to.
In matchplay a hole is a hole. When the higher handicapper makes a nine it costs him one hole; when you make a six it costs you one hole. Giving the full difference hands him the upside of his bad golf without the downside. In strokeplay the effect reverses, because there every one of those extra shots stays on the card.
The spread of your hole scores, not their average. A wild player and a steady player with the same handicap shoot the same number over a season and win completely different matches. Wildness wins you more blowouts and loses you more tight ones.
Real. Every run plays 180,000 individual holes in your browser, scoring each one from a distribution built off the two handicaps, then counts the results. Run it twice and the numbers will move slightly, because that is what probability looks like when nobody is rounding it for you.