The Caldwell Cup logoThe Caldwell CupEst. 2003
Aerial view of Hole 9 at the Palmer Course

XXIII · October 8–10, 2026

The
Caldwell
Cup

Fourteen men who met in Chapel Hill, one trophy that has traveled the Carolinas since 2003, and a jacket nobody is allowed to dry clean.

View the RecordsCup History
Years Played
23
Contenders
14
This Year
Reunion

Reigning champion leads the roll

Last 5 Cup Champions

Full roll of honor →

  1. Reigning Champion

    2025

    Robert Orr

    McLemore Resort

    Rising Fawn, GA

    101B

  2. 2024

    Brad Friedman

    Reunion Resort

    Orlando, FL

    103A

  3. 2023

    Dan Valenti

    Reunion Resort

    Orlando, FL

    103A

  4. 2022

    Robert Orr

    Fripp Island Resort

    Fripp Island, SC

    101B

  5. 2021

    Robert Orr

    Fripp Island Resort

    Fripp Island, SC

    101B

The Handicap Board

All 14 contenders · updated before every round

1Clark2.8
2Jeff6.2
3Barrett8.4
4Robert10.2
5Jeremy11.3
6Brandon12.0
7Stamati13.5
8Dan18.3
9Bill19.2
10Kevin32.6
11Brad36.7
12PenSCR
13ScottSCR
14JohnSCR

Low index: Clark Avery (2.8) · Field average 15.6

The Scrapbook

Pictures Over the Years

CC VIII — Shaw's near hole-in-one
CC XIII — SHAWN in tees
Shaw's near hole-in-one at CC VIII
Pictured: the closest anyone has come to a hole-in-one during any round of the Caldwell Cup — Kevin Hinshaw, during the team play portion of CC XIV.

Still unclaimed

Hole-in-One Pot

$1,350

Estimated par 3 shots thru 23 Cups
4,414*
Aces recorded
0

Every man pays into the pot each year. The first ace in competition takes the whole thing — until then it keeps growing.

*Estimate assumes four par 3s per round across the full field.