Sailor · 2012–2026

Bob Cunningham

south carolina yacht club PHRF handicap Harbor 20 College fleet racing

Search sailors · About these ratings

Events: 30
Win rate: 0%
Podium rate: 30%
Typically beats: 36%
Best class ranking: #219

Nemesis: James Lilyquist
Rival: Sophie Grigg
Signature result: 2nd of 8

Partnerships · 30 sailors

Claire Calkins · University of Virginia (Wahoos 2), University of Virginia (Wahoos) · College fleet racing 2events 0 wins together · 0 podiums · 2 events · 1 of 44 races won Beat 25% of the fleet together · best 6th · Sep 2025 – Oct 2025
Mark Berns · Dow Jones · J/30 2events 0 wins together · 1 podiums · 2 events · 1 of 13 races won Beat 42% of the fleet together · best 3rd · May 2014 – Sep 2014
Mason Chapman · University of Virginia (Wahoos) · College fleet racing 2events 0 wins together · 0 podiums · 2 events · 0 of 56 races won Beat 17% of the fleet together · best 12th · Sep 2025 – Oct 2025
Seth Shepard IV · Dow Jones · J/30 2events 0 wins together · 1 podiums · 2 events · 1 of 13 races won Beat 42% of the fleet together · best 3rd · May 2014 – Sep 2014
Daniel Meeson · Dow Jones · J/30 2events 0 wins together · 1 podiums · 2 events · 1 of 13 races won Beat 42% of the fleet together · best 3rd · May 2014 – Sep 2014
Daniel Renn · Dow Jones · J/30 2events 0 wins together · 1 podiums · 2 events · 1 of 13 races won Beat 42% of the fleet together · best 3rd · May 2014 – Sep 2014
Shawn Bay · Tacktile · PHRF handicap 2events 0 wins together · 2 podiums · 2 events · 0 of 2 races won Beat 68% of the fleet together · best 2nd · Aug 2025 – Oct 2025
Jeffrey Wilson · Tacktile · PHRF handicap 2events 0 wins together · 2 podiums · 2 events · 0 of 2 races won Beat 68% of the fleet together · best 2nd · Aug 2025 – Oct 2025
Benjamin D’Amico · University of Virginia (Wahoos) · College fleet racing 1events 0 wins together · 0 podiums · 1 events · 0 of 26 races won Beat 13% of the fleet together · best 14th · Sep 2025 – Sep 2025
Jim Farrell · Tacktile · PHRF handicap 1events 0 wins together · 1 podiums · 1 events · 0 of 1 race won Beat 75% of the fleet together · best 2nd · Aug 2025 – Aug 2025

Lift shows how much better this sailor finishes with that partner aboard.

Rating history

— Helm rating, all classes · - - Crew rating, all classes

Event history · 30

Date	Event	Boat	Class	Role	Finish
2 May 2026	DeSole Cup	Bluefish	Harbor 20	Skipper	6th / 14
18 Oct 2025	Luce Trophy	University of Virginia (Wahoos)	College fleet racing	A Crew (5,7-15)	12th / 15
11 Oct 2025	70th Annual Indian Harbor Stratford Shoal Race - the Gearbuster	Tacktile	PHRF handicap	Other	3rd / 6
4 Oct 2025	Ocean Challenge	Bluefish	Harbor 20	Skipper	10th / 11
27 Sep 2025	Jefferson Cup	University of Virginia (Wahoos 2)	College fleet racing	B Skipper (1-2,5-7)	6th / 8
6 Sep 2025	Riley Cup	University of Virginia (Wahoos)	College fleet racing	A Crew (1-6,9-13)	14th / 16
29 Aug 2025	2025 Vineyard Race	Tacktile	PHRF handicap	Other	2nd / 5
12 Jul 2025	2025 Vineyard Cup Regatta	Silhouette	PHRF handicap	Crew	5th / 9
3 May 2025	DDS&A Cup	Bluefish	Harbor 20	Skipper	13th / 15
4 May 2024	Windmill Harbour and DDS&A Cup	Bluefish	Harbor 20	Skipper	13th / 15
7 Oct 2023	Ocean Challenge	Bluefish	Harbor 20	Skipper	8th / 12
7 Jul 2023	2023 Vineyard Cup Regatta	Ruffian	PHRF handicap	Other	3rd / 8
6 May 2023	Windmill Harbour and DDS&A Cup	Bluefish	Harbor 20	Skipper	13th / 14
8 Oct 2022	Ocean Challenge	Bluefish	Harbor 20	Skipper	9th / 13
9 Jul 2022	2022 Vineyard Cup Regatta	Ruffian	PHRF handicap	Other	2nd / 7
23 Jun 2022	2022 Edgartown Race Weekend 'Round-the-Sound Races	Ruffian	PHRF handicap	Other	2nd / 5
22 Jul 2021	2021 Edgartown Race Weekend, 'Round the Buoys	Ruffian	PHRF handicap	Other	3rd / 5
10 Jul 2021	2021 Vineyard Cup Regatta	Ruffian	PHRF handicap	Other	2nd / 8
12 Jul 2019	2019 Vineyard Cup	Ruffian	PHRF handicap	Other	3rd / 11
15 Sep 2018	2018 Back to School Regatta/Dinghy Challenge Cup and Viper 640 Gulf Coast Championship	11909	Optimist	Skipper	9th / 9
9 Sep 2017	2017 HYC Great Chase Race	Ruffian	Handicap	Skipper	19th / 23
8 Jul 2017	2017 Vineyard Cup	Ruffian	PHRF handicap	Other	7th / 12
27 May 2017	Commo. Juby Wynne Memorial One Design Regatta	11909	Optimist	Skipper	6th / 9
16 Oct 2016	Closing Regatta	TBD	06 Opti Green	Skipper	13th / 17
12 Sep 2014	2014 J 30 North American Championship	Dow Jones	J/30	Headsail Trimmer	9th / 13

Ratings

Class	Rating	Rank	Adj. ±
All classes Helm	54 provisional	#41043 band 28536–55242	—
Harbor 20 Helm	-8 provisional	#219 band 142–258	—
All classes Crew	-62 provisional	#52174 band 39193–59971	—

5 more classes, not yet ranked

College fleet racing · Crew · 21 races, 2 events · rating -118
Optimist · Helm · 16 races, 2 events · rating -173
J/30 · Crew · 13 races, 2 events · rating 28
College fleet racing · Helm · 5 races, 1 event · rating -49
06 Opti Green · Helm · 4 races, 1 event · rating -6

Rank among sailors with ten or more rated races over three or more events, all time. In brackets, the ranks this rating cannot be told apart from. Adj. ± is the adjusted plus-minus in points of fleet beaten.

Helm and crew

As helm	23 events	0 wins	beats 41%
As crew	7 events	0 wins	beats 43%

Positions: A Crew (5,7-15) (1) · B Skipper (1-2,5-7) (1) · A Crew (1-6,9-13) (1) · Headsail Trimmer (1)

How they race

Closer	+14 pts	last race of an event vs. the rest
Comeback	−3 pts	the race after a bottom-half finish
Consistency	51%	100% = the same result every event
Small fleets (<12)	51%	of the fleet beaten

Head to head

Helm	Races	W–L
James Lilyquist	70	14–56
Barrett Lhamon	56	8–48
Eleanore De Sole	43	4–39
Eric Norman	41	5–36
Sophie Grigg	40	20–20
Domenico De Sole	40	3–37
Charlotte Stillman	40	17–23
Gordon Miller	38	21–17
David Downey	32	14–18
Eli Leopold	30	11–19
Eva DeCastro	30	1–29
James Fair	30	0–30

Most-beaten opponent: Alexander Pfeffer (23–4).

Seasons

Year	Events	Beat
2026	1	62%
2025	8	34%
2024	1	14%
2023	3	39%
2022	3	64%
2021	2	68%
2019	1	80%
2018	1	0%
2017	3	34%
2016	1	25%
2014	3	44%
2013	2	45%
2012	1	17%

Boats

Ruffian · PHRF handicap, Handicap · 12 events · 2012–2023
Bluefish · Harbor 20 · 7 events · 2022–2026
University of Virginia (Wahoos) · College fleet racing · 2 events · 2025
Tacktile · PHRF handicap · 2 events · 2025
11909 · Optimist · 2 events · 2017–2018
Dow Jones · J/30 · 2 events · 2014
University of Virginia (Wahoos 2) · College fleet racing · 1 events · 2025
Silhouette · PHRF handicap · 1 events · 2025
TBD · 06 Opti Green · 1 events · 2016

Where they race

Vineyard Haven, MA, USA · 8 events
Hilton Head Island, SC · 4 events
Hilton Head Island , SC · 3 events
Edgartown, MA, USA · 2 events
Preliminary Results · 2 events
Westport, CT, USA · 2 events

Is this you?

Claim it to merge duplicates and remove results that aren’t yours. Changes apply at the nightly rebuild.

Helm rating across all classes: 54 (±153), #41,043.Crew rating across all classes: -62 (±186), #52,174. Compiled from public results; not an official ranking.