Ten Matches, Match by Match

Red's roster is the older and higher one again, so the strokes flow that way: in the morning Four-Ball, Red's players collect 60 shots to Blue's 48, and in the afternoon Red's sides get 17 to Blue's 11. Red also has the two lowest handicaps in the field, Jimmy Gurney and Rick Gordon at 7, while Blue answers with four 8s: Bob Walters, Bill George, Ron George and Adam Hackett. Here's how the ten look against what the record book says.

Four-Ball

Match 1 — Blake & Waldron vs. DeAngelis & Ron George Sr. John Waldron's first tee shot in the Cup comes with eight strokes in his pocket and Roger Blake, a 21 in each of his three appearances, alongside him. Across the tee is the winningest player in Cup history: Jon DeAngelis has 50 wins, is 7–2–1 since 2022, and at 11 he matches the lowest number of his 32 Cups — meaning he gives shots to everyone in this match while his partner takes 13. DeAngelis and Ron George Sr. have been paired four times, going back to 2007, and are 2–2–0.

Match 2 — Adam Hackett & Bill George vs. Gurney & Jabbari. The quiet grudge match. Bill George and Jimmy Gurney have been on opposite sides thirteen times, Gurney ahead 7–5–1, and they've played singles in three of the last five Cups; last October it was George who came out on top in what the recap called a match with a lot of great shots by both players. Gurney arrives at a career-best 7 and plays the whole match off scratch. Jordan Jabbari makes his debut with five shots, and the Blue pair, together once before in 2023, gets one apiece.

Match 3 — Juday & Walters vs. Bres & Hackett. Tom Bres and Dennis Hackett are the second-best partnership in Cup history at 7–2–0 over nine outings stretching back to 1994, though the fine print matters: they are 6–1 in Foursomes and only 1–1 in Four-Ball. Brad Juday and Bob Walters have played together exactly once, in 2002, and won. The personal ledgers run deep here — Juday and Bres have met sixteen times, five in singles, with Juday up 8–7–1, while Hackett leads Juday 9–6–2 across seventeen. Walters, at his career-low 8, is the only man in the match without a stroke.

Match 4 — Peggs & Bass vs. Grace & Frank George. A partnership coming out of storage: Jamie Grace and Frank George were a regular pair between 1999 and 2013, going 3–2–1, and haven't teamed since. They take 22 shots between them from a Blue pair that has played together once, in 2020, and lost. Glenn Peggs plays off scratch and owns the head-to-head against Frank George at 3–1.

Match 5 — Williams & Ron George vs. Gordon & Haas. The longest-running act in the field: Mark Williams and Ron George have been partners nine times since 1995 and are 5–3–1, the best mark of any Blue pair this Saturday. Williams also takes 14 shots, the most anyone gets all day. They meet the toughest out in the morning: Matt Haas is 14–5–2 for his career and a perfect 6–0–1 in Four-Ball, and he has beaten Ron George in five of their six meetings. Gordon, at 7, plays off scratch.

Foursomes

Match 6 — Blake & Waldron vs. Gurney & DeAngelis. The widest gap of the weekend: 40 combined for Blue against 18 for Red, which hands the Blue pair 11 shots in alternate shot. That is a lot of holes to give, but Foursomes is where strokes are hardest to use, and the Red pair has DeAngelis, who has played 30 of them. Gurney and DeAngelis have been paired twice, in 2016 and 2017, splitting.

Match 7 — Adam Hackett & Bass vs. Jabbari & Grace. The only rematch of a current partnership: Hackett and Bass played alternate shot in both 2024 and 2025, winning one and losing one. Jamie Grace, in his 32nd Cup and missing only 2024, brings the rookie along with six shots on the card.

Match 8 — Ron George & Peggs vs. Ron George Sr. & Haas. Father against son. They have been on opposite sides sixteen times, the son ahead 9–4–3, and the one time it came down to singles, in 1999, he won. Peggs is quietly at his best in this format at 7–3–0, and the Blue pair won their only outing together in 2019. Red take seven shots, all of them courtesy of Senior's 24.

Match 9 — Juday & Bill George vs. Hackett & Bres. Now Bres and Hackett are in their element: 6–1–0 as a Foursomes pair, and they get four shots on top. Juday and Bill George have teamed once, in 2017, and lost, and Juday's form has been thin lately — 1–4–4 since 2022. If Red is going to build a lead before Sunday, this is the match the form book points to.

Match 10 — Walters & Williams vs. Frank George & Gordon. No strokes anywhere: 29 against 28, the closest-matched pairing of the day. It's also the only true rematch, and Blue won it in 2024. Frank George and Rick Gordon are the fourth-best partnership in Cup history at 5–1–1; Walters and Williams have been paired seven times since 2010 and sit 3–3–1. Williams and Frank George have faced each other fourteen times and are dead level at 6–6–2, which feels about right for a match with nothing between the sides.

One number worth keeping in mind on Sunday morning: in the 26 Cups where one side led after Saturday, that side went on to win 22 times, and only three have ever been overturned on the final day.

Bob Goes Down, Vinnie Goes Up: Reading the 2026 Handicap Sheet

Twenty-one players, an average handicap of 13.7, a median of 11, and a spread from Rick Gordon and Jimmy Gurney at 7 to Ron George Sr. at 24. That's the 2026 field, and it's the highest field average since 2017. Three years ago the Cup average bottomed out at 11.4, the lowest in the event's history; it has climbed back every year since. Nearly a quarter of this year's field is a 20 or higher, the largest share since 2015, even while 38 percent are still single digits. The middle is disappearing: this is a field of low handicaps and high ones.

The headline mover is Bob Walters. In 2018 he played off 21, his career worst. Since then it has gone 16, 16, 15, 11, 10 and now 8 — the lowest number of his 26 Cups, and eight strokes better than he was in 2021. Nobody in the field has moved that far in that direction. His career average is 15.5, so the man teeing it up this October is playing about seven strokes better than his own career norm.

Running the other way is Vince Olenik. Vinnie arrived in 2001 at a 3 and got to a 2 in 2002, and for years he was the scratch-level yardstick everyone else was measured against; his career average of 5.9 is still the lowest of anyone in this year's field. He comes in at 11 this time, the highest of his 25 Cups. It's a gentle slope — 10, 10, 10, 11, 9, 11 across the last six — but the direction is unmistakable, and the strokes are starting to flow the other way.

They're not alone in either direction. Jimmy Gurney is at 7, his best ever and eight shots better than the 15 he brought to his first Cup in 2016. Jon DeAngelis, in his 32nd Cup, matches the best number of his career at 11, first set back in 1996. Will Bass has gone 21 to 11 since 2018, and Rick Gordon keeps hovering around his 2023 career low of 5. On the other side of the ledger, Brad Juday has drifted from 15 in 2021 to 19 now, Mark Williams has sat at 21 for three straight years, and Frank George is back up to 21 after an 18 last fall.

The longest arc in the data belongs to Dennis Hackett. He played the first Cup in 1994 off a 7. Thirty-one Cups later he's a 15, having touched 16 in 2022. Tom Bres has gone the other way lately, 24 in 2024 down to 20 now, and Ron George Sr., first seen in 1997 at 17, has settled in at 24 for the third year running. Meanwhile Ron George, the only man to play all 33 Cups, has barely budged: 13 as a rookie, 7 at his best in 2012, and an 8 this year.

Four players in this field weren't here last fall. Matt Haas returns at 8 after sitting out 2025, close to the 6 he carried in 2023. Roger Blake is back for his third Cup, and remarkably he has been a 21 in every one of them — 2021, 2024 and 2026. The two newcomers are John Waldron at 19 and Jordan Jabbari at 12, which lands Jabbari right on the field's median. Seven players from last year's rosters aren't in this one, and the field has shrunk from 24 to 21.

By team, Red carries the higher average at 14.2 to Blue's 13.2, so on balance the strokes will flow from Blue to Red. History says Blue shouldn't mind. Across every Cup match ever played, players at 9 or better have won 53 percent of the time and those at 20 or above just 45 percent, with the 15-to-19 group at 48. The strokes narrow the gap; they don't erase it. Which is worth remembering when the pairings go up and somebody complains that he's giving away too many.