Cup Week Reality Check: When I Lost Money But The System Kept Winning

Cup Week Reality Check: When I Lost Money But The System Kept Winning
My Cup Week Reality...

Episode 13 of The Grind is live, and it's the most honest breakdown I've ever done.

Look, I'm not going to bury the lead here. Melbourne Cup Week 2025: I lost money.

Not because the system failed. Because I broke my own rules.

But here's what's interesting - and why this episode matters more than any winning one I've done - the package clients who followed the staking plan? 17.2% ROI across the four days.

Let me show you exactly what happened.

The Cup Week Breakdown

Derby Day (Day 1):

  • 38 bets, 7 winners
  • -19% ROI
  • Not the start we wanted

Melbourne Cup Day (Day 2):

  • 56 bets, 16 winners, 28% strike rate
  • +15% ROI on the tips
  • But I overstaked the Cup. Bet up. Did my ass.
  • This was separate business for me - Broncos Grand Final winnings going into the Cup
  • Conscious decision, prepared to lose it
  • Lost it

Oaks Day (Day 3):

  • 10 bets, 5 winners
  • +87% ROI
  • The bounce back

Champions Day (Saturday):

  • 34 bets, 10 winners
  • +34% ROI
  • On the wet track at Flemington

The Four-Day Reality

Package Results (To Win $200, Max Bet $100):

  • Total Bets: 138
  • Winners: 38
  • Outlay: $7,687
  • Return: $9,013
  • Profit: $1,326
  • ROI: 17.2% at high price

My Personal Results: Lost.

Why? Because I:

  1. Overstaked the Melbourne Cup (separate from system)
  2. Laid a few winners that came in
  3. Didn't get the luck

But here's the thing - the system worked. The official tips delivered. The staking plan delivered. The process delivered.

I just broke my own rules on one race and paid for it.

Why This Matters More Than A Winning Week

Anyone can show you winners. I can cherry-pick my best days and look like a genius.

But this? This is what professional punting actually looks like:

  • The system can be right while you're wrong
  • Breaking rules costs you
  • Staking discipline matters more than selection quality
  • Variance is real and unavoidable

The real story isn't Cup Week. It's the journey since June 12.

The Complete Journey (No Hiding)

Let me show you the monthly breakdown since we launched:

June (June 12-30): +13% Strong start. Feeling good.

July (Full Month): -6% Bit of a snag. Up and down. Couldn't get going.

Early August (First 2 Weeks): -24% 159 bets. 19 winners. Lost $2,400 betting to win $200.

This was the hell I told you about. Two months of losing. Sitting in this chair every day, fronting up, knowing it would turn. Everyone asking "when will it turn?"

I said: "I know it will. I've been here before."

Late August (Next 2 Weeks): +20% 295 bets. 78 winners.

There it is. The turnaround. Exactly like I said.

September: +5% Back on track. Not shooting lights out, but steady.

October: +7% Building momentum.

November (So Far): +14% 185 bets, 52 winners, 28% strike rate.

The system is heating up exactly when I said it would.

What Episode 13 Covers

I go deep on:

1. Complete Cup Week Analysis Every race that mattered. Weeping Woman firming with high weight. Pride of Jenny's pattern (11th, 9th, 10th, 7th first-up - all failed). The plays that worked and the ones that didn't.

2. The Monthly Variance Map The actual numbers from June to November. The -24% hell. The +20% recovery. The steady climb. This is what variance looks like at volume.

3. Favorites Analysis Since 2018 Every metro and provincial track. Which tracks murder favorites (Moonee Valley night: -9.7%). Which tracks favor them (Cranbourne: +6%, Moonee Valley day: +6.9%, Sandown Lakeside: +7%).

Ascot, Belmont, Canterbury, Caulfield, Flemington, Randwick - I run through them all with sample sizes since 2018.

4. Jockey Edge Testing Does following jockeys actually work?

I tested every major jockey on favorites since 2018. Sample sizes over 200 rides minimum.

Some results:

  • Nash Rawiller: +13% (always been a money jockey)
  • Noel Callow: +20% (on fire)
  • Linda Meech: +7% (underrated)
  • Willie Pike: -6% (market prices him perfectly)
  • Damian Oliver: -8%
  • James McDonald: -3.88% with 40% strike rate over 1,111 rides

The market is very good at factoring in jockey ability. Easy to criticize jockeys. Hard to profit from following them.

5. Pattern Recognition How to read form for what's coming next, not just what happened. Pride of Jenny failing the Champions Mile again - pattern was there. Weeping Woman defying predicted pace negative at 1100m - market trusted the class edge.

The Real Lesson From Cup Week

I lost money because I broke my preparation.

I had my staking plan: To win $200, max bet $100. But on the Cup? I bet up. Separate business, separate decision, but still broke my own framework.

The clients who followed the plan? Made 17.2%.

That's not luck. That's preparation.

Preparation is so important. When you're ready to bet before race one, you expect to win. Your head's in the right space. You're not making emotional decisions. You're executing a plan.

Without preparation:

  • Making decisions during races (emotional)
  • Breaking own rules (guilty)
  • Taking wrong prices
  • Chasing losses

With preparation:

  • Rules already set
  • Staking predetermined
  • Selection process defined
  • Crisis response ready
  • Price shopping strategy established

I had the preparation. Then I consciously chose to break it on one race. That's on me.

But the system kept working. That's the point.

What's Next

November is sitting at +14% through the first week.

The improvements I made during that August losing streak are paying off:

  • First-up horses: +32% ROI (majority of profit)
  • Heavy tracks: +6.8% with selective volume
  • Daily manual review: eliminating queries
  • Good value factor: +10.6% with Selection 1

The system is getting sharper. October was +7%. November is +14% so far. The trajectory is there.

Process over results. Always.

Watch Episode 13

I break all of this down with the actual data on screen. No hiding. Complete transparency. This is what professional punting looks like on the hard days.

Watch here: https://youtu.be/yFmop7qlBM4

And look - if you're going through a losing run right now, watch this. Because the -24% two weeks? I got through it. The system got through it. You can too.

You just have to keep grinding. Face the mirror. Do the work. Trust the process.

This is a long, long game.

The hard work never stops.

— Kingsley

P.S. If you want feedback on your own approach or have questions about anything in Episode 13, drop them in the YouTube comments. I read every single one and I'll answer what I can. The more we share information, the better punters we all become.