I really enjoy match play, but part of me hesitates to give advice about it, because overthinking can backfire. Whether I'm playing in a competition like this month's Ryder Cup or a low-key eighteen with a friend, my general approach is pretty simple: First hit the ball in the fairway, then try to hole every shot. The quicker you can get the ball in the cup the better, because absolutely anything can happen in match play—and usually does.
As an example, let's say you decide to play it safe after your opponent misses a green. Fine, but then he chips in for birdie and suddenly you're left with a thirty-foot putt over a hump to halve the hole. Even if he just chips it close for a tap-in par, you've still got a very testy two-putt to salvage a draw. Far better to think win, win, win on every shot. This mentality also makes match play more fun. Trying to put the ball in the hole every time you step up beats the heck out of competitive stroke play, where you have to pay more attention to where your misses end up.
I've won my share of match play events over the years (presumably that's why I was picked to captain the 2008 European Ryder Cup team) and have learned a number of things that might be helpful, even in everyday matches. I'll share them with you, but remember not to get too cute or stray from my core principles, stated above.
One of the toughest lessons to learn is to avoid slacking off when you've got the lead. There's a tendency to get protective, especially when you're a few holes up, but discipline yourself to keep thinking of each hole as a new match, and try hard to go up by one more. You can't afford to think, "Well, that's okay, I've got a cushion," because in match play momentum can turn on a dime. Three up may sound nice, but if you lose the next hole, then you're only two up and negative thoughts have a way of cropping up ("Things are going the wrong way!"), and one up is nothing in match play. If you get in trouble on a hole, fight like hell to get back in it. Even if it seems hopeless, at least try to force your opponent to make a putt for the win—he might just miss. In short, never let up and never give up.
Another rule: Don't take unnecessary risks. A lot of people seem to think of match play as an opportunity to go for every shot they could conceivably pull off, figuring that's the best way to win holes in a tight match and that the price of failure is merely the loss of one hole. Yes, risks are sometimes warranted in match play, but usually only when you are behind late in the game and there's nothing to lose. In fact, you'll win the most holes by relentlessly keeping the pressure on your opponent and letting him make the mistakes, not by catching lightning in a bottle with the occasional brilliant shot. You're always better off staying in the hole than being in your pocket. That's why I feel you should only attempt shots you are certain, or almost certain, that you can pull off. If you're not comfortable with a shot, put that club back in the bag and try something else.
These principles established, let's walk through a match and look at some other strategies.
Before the Match Begins Make sure you are warmed up and ready to compete. In stroke play there may be some latitude to ease into a round until you get your rhythm, but in match play you need to be ready to win holes coming out of the gate. A win on hole number one could be the difference in the match. In particular, practice those two- and three-foot "gimme" putts that you may not be used to having to hole in casual play, and spend extra time working on your short game. Nothing is more likely to rile your opponent psychologically than your ability to repeatedly get up and down, pulling out halves or wins like a magician pulling rabbits from a hat.