When to Press: Advanced Nassau Strategy

Pressing is where Nassau gets interesting. A press creates a new bet running parallel to the original, giving you a chance to recoup losses or extend your lead. Done strategically, pressing wins matches. Done emotionally, it compounds losses.

Understanding when to press, when to accept a press, and how to manage multiple bets separates Nassau veterans from beginners.

What is a Press?

A press starts a new bet at the same stakes as the original, beginning from the current hole. The original bet continues, and the press runs alongside it until the end of that nine or 18 holes.

Example:

• You are playing $10 front nine Nassau
• After 4 holes, you are 2-down
• You press, creating a new $10 bet starting from hole 5
• Now you have two bets running: the original (which you are losing) and the press (starting fresh)

If you win the press 2-up from holes 5-9, you win $20 on the press but still lose the original bet. Net result: Even.

If you lose both, you are down $20 total on the front nine.

Automatic Press Rules

Many groups play automatic presses to remove the decision-making. Common auto-press triggers:

2-Down Auto-Press: When you fall 2-down in any bet, a press automatically starts. This is the most popular rule.

Example:

• Original front nine bet starts
• You lose holes 1 and 2, now 2-down
• Press automatically activates starting hole 3
• You win holes 3 and 4, now only 1-down on original, but 2-up on press

3-Down Auto-Press: More conservative, gives players more room before pressing.

1-Down Auto-Press: Aggressive, creates many bets. Can get confusing fast.

No auto-press: Players choose when to press. Requires clear verbal declaration ("I am pressing").

Clarify auto-press rules before starting the round. Nothing derails a Nassau faster than "I thought we were auto-pressing at 2-down" arguments on hole 7.

When to Press Strategically

Press when you are 2-down or 3-down and feel you are playing solid golf. If you hit a few good shots that just did not fall, but your opponent got lucky, pressing makes sense. You are likely to turn it around.

Press when your opponent shows cracks. They won the first few holes but started spraying drives or missing putts. Momentum is shifting. Lock in a press while you have the edge.

Press on holes that favor your game. If you are long off the tee and the next few holes are wide-open bombers, press. If you are a great short-game player and the next stretch has tight greens, press.

Press when the math works. If you are 3-down with 5 holes left, you probably will not win the original bet. But you can win a press starting fresh over those 5 holes.

When NOT to Press

Do not press emotionally after a bad hole. You chunk one in the water, lose the hole, go 2-down, and immediately want to press. This is ego, not strategy. If your game is falling apart, pressing compounds losses.

Do not press when your opponent is on fire. They just made three straight birdies and you are scrambling for pars. Wait until they cool off before pressing.

Do not press if you cannot afford the risk. Presses double your exposure. If you are already at your comfortable loss limit, do not press.

Do not press late if you are already winning. You are 3-up with 3 holes left. Your opponent presses. You do not need to counter-press. Just close out the original bet.

Managing Multiple Presses

The complexity trap: Original bet, first press, second press, opponent's press. Suddenly you are tracking 4 separate bets on the back nine.

Strategy for multiple bets:

1. Track status after every hole. Use a scorecard or app to note current standing on each bet.

2. Prioritize the biggest deficit. If you are 3-down on original but 1-up on a press, focus on not blowing up the original further.

3. Know when to stop pressing. Adding a third press with 3 holes left is rarely smart. You are likely chasing losses at that point.

4. Accept that you might win some and lose some. The goal is net positive, not winning every bet.

The Counter-Press

When your opponent presses, you can counter-press (also called a re-press). This creates another new bet, again doubling the action.

Example:

• Original $10 bet, you are 2-up
• Opponent presses, creating new $10 bet starting now
• You counter-press, creating another $10 bet starting now
• Now three bets running: original (you winning), their press, your counter-press

When to counter-press: You feel confident and want to maximize profit from your hot streak.

When not to counter-press: You are winning the original and do not need the risk. Let them chase.

Ego check: Counter-pressing is often about ego ("I will take your press and raise you"). Make sure it is strategic, not emotional.

Press Strategies by Position

When losing: Press at 2-down if you are playing well. Press at 3-down if you have favorable holes coming up. Do not press at 4-down or 5-down unless you have a miracle run in you.

When winning: Generally, do not press. You are already winning. Exception: opponent looks like they are falling apart and you want to capitalize.

When tied: Pressing from tied is aggressive. Only do it if you feel you are about to go on a run and want to lock in extra profit.

Pressing in Team Nassau

In team formats (partners), pressing requires communication. Both partners should agree before pressing.

The danger: One partner wants to press, the other is struggling. Pressing creates more pressure on the weak link.

The opportunity: Your team is 2-down but your partner just found their rhythm. Press together to recoup losses.

Rule of thumb: If both partners feel confident, press. If one is uncertain, do not.

Psychological Factors

Pressing signals confidence. When you press, you are telling your opponent "I am coming back." This can be intimidating or motivating depending on personalities.

Accepting a press signals acceptance. If you do not counter-press, you are acknowledging the new bet without escalating. This keeps things manageable.

Rejecting a press (if allowed): Some groups allow you to decline a press. This is rare but removes the forced escalation dynamic.

The tilt factor: If your opponent is pressing every time they go down, they might be tilting. Stay calm, focus on your game, and let them compound mistakes.

Common Press Mistakes

Mistake 1: Pressing too early. You are 1-down after 2 holes. Relax. Plenty of golf left.

Mistake 2: Pressing too late. You are 4-down with 2 holes left. A press will not save you at this point.

Mistake 3: Not tracking bets. By hole 16 no one remembers what bet started when or who is up on what. Write it down.

Mistake 4: Pressing on tilt. You are frustrated, playing poorly, and keep pressing hoping to turn it around. This is how you lose $100 instead of $20.

Mistake 5: Over-complicating with too many presses. Keep it to one or two presses max. Beyond that, math gets messy and focus deteriorates.

Settlement with Multiple Presses

At the end of the nine or 18 holes, tally each bet separately:

Example back nine:

• Original bet: You 1-up, win $10
• First press (started hole 5): Opponent 2-up, you owe $10
• Second press (started hole 8): You 1-up, win $10
• Net: You win $10 total

Use apps or scorecards to track. Mulligan Money (launching Spring 2026) tracks multiple Nassau bets and presses automatically, showing live standings and final settlement.

Advanced Press Variations

The "Greenies" Press: If someone gets closest to pin on a par 3, they can force a press. Adds another strategic layer.

The "Birdie Press": Make a birdie and you can press for free (no risk if you lose the press, double payout if you win). Rewards great golf.

The "Side Press": Run a separate press that only counts on odd holes or even holes. Gets complicated but adds variety.

Press Etiquette

Announce presses clearly. Say "I am pressing" or "Press" loudly so everyone hears. Do not mumble it then claim later you pressed.

Respect auto-press rules. If the group agreed on auto-press at 2-down, do not argue when it triggers.

Do not mock opponents for pressing. They are creating more action. If you do not want the press, that is fine, but respect their decision.

Do not slow play debating presses. Make the decision quickly. Pressing should add excitement, not delay the round.

When to Simplify

If presses are creating confusion, stress, or arguments, simplify:

• Go back to basic Nassau with no presses
• Limit to one press per nine
• Only allow presses at specific holes (like the turn)

The goal is fun, competitive golf betting. If presses are ruining that, remove them.

The Bottom Line

Pressing is a powerful Nassau tool when used strategically. Press at 2-down or 3-down when you are playing solid golf and momentum is shifting. Avoid emotional revenge presses after bad holes.

Track all bets carefully, limit presses to manageable numbers, and know when to stop. Pressing should give you a chance to recover or extend leads, not dig deeper holes.

Join the Mulligan Money waitlist for early access to automatic press tracking, real-time bet status, and simplified Nassau settlement when our app launches Spring 2026.

Master the press, and Nassau becomes a dynamic strategic game that keeps every match competitive through 18 holes.