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Sailor · 2015–2025

Anna Groszkowski

ssa College fleet racing420Optimist

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Events
36

386 races · 44 race wins

Win rate
11%

11% win rate · 4 of 36

Podium rate
17%

6 top-three finishes

Typically beats
48%

of boats faced (range 46%–51%, 1,127 boats)

Best class ranking
#4486

Helm in Optimist · rating 96

Longest win streak
7

race wins in a row

Most successful partnership
Maxwell Penders

2 wins · 2 podiums in 3 events together

Biggest lift
Iliana Vasslides

+41 points of fleet beaten when sailing together

Longest-running crew
Connor Lothrop

Mar 2023 – Apr 2024 · 5 events

Nemesis
Bridget Green

7–72 head to head in 79 races

Rival
Ava Farley

40–37 in 77 races

Best day
29 Mar 2025

1-1-5-4-3-1-2-1-1-1-2-1-2-2-1-2-3-1-1-1-2-5-1-3 · W&M Spring Open

Signature result
1st of 34

2021 Sandy MacVickar Regatta · 420 · 1 Jan 2021

Partnerships · 31 sailors

Most successful partnership: Maxwell Penders — 2 wins · 2 podiums in 3 events together
  • Connor Lothrop · University of Virginia (Wahoos) · College fleet racing 5events 2 wins together · 2 podiums · 40% win rate · 25 of 98 races won Beat 46% of the fleet together(−2 vs. without) · best 1st · Mar 2023 – Apr 2024
  • Addison Lisiewski · 8094, Anna Groszkowski · 420 4events 1 wins together · 1 podiums · 4 events · 1 of 35 races won Beat 62% of the fleet together(+16 vs. without) · best 1st · Jan 2021 – Jul 2021
  • James Unger · University of Virginia (Wahoos) · College fleet racing 4events 1 wins together · 1 podiums · 4 events · 8 of 68 races won Beat 34% of the fleet together(−16 vs. without) · best 1st · Nov 2023 – Apr 2024
  • Laura Rhodes · University of Virginia (Wahoos) · College fleet racing 4events 0 wins together · 0 podiums · 4 events · 0 of 90 races won Beat 10% of the fleet together(−43 vs. without) · best 10th · Oct 2022 – Jan 2024
  • Maxwell Penders · University of Virginia (Wahoos) · College fleet racing 3events 2 wins together · 2 podiums · 3 events · 20 of 64 races won Beat 67% of the fleet together(+21 vs. without) · best 1st · Apr 2024 – Mar 2025
  • Lila Gibson · University of Virginia (Wahoos) · College fleet racing 3events 1 wins together · 1 podiums · 3 events · 12 of 73 races won Beat 42% of the fleet together(−7 vs. without) · best 1st · Oct 2022 – Mar 2025
  • Lydia Sweeney · University of Virginia (Wahoos 2), University of Virginia (Wahoos) · College fleet racing 3events 1 wins together · 1 podiums · 3 events · 17 of 61 races won Beat 44% of the fleet together(−4 vs. without) · best 1st · Oct 2022 – Apr 2023
  • Iliana Vasslides · University of Virginia (Wahoos) · College fleet racing 3events 1 wins together · 2 podiums · 3 events · 12 of 23 races won Beat 86% of the fleet together(+41 vs. without) · best 1st · Apr 2024 – Apr 2025
  • Brooke Davi · University of Virginia (Wahoos 2), University of Virginia (Wahoos) · College fleet racing 2events 0 wins together · 0 podiums · 2 events · 0 of 30 races won Beat 15% of the fleet together · best 6th · Oct 2022 – Jan 2024
  • Andrew Montague · University of Virginia (Wahoos) · College fleet racing 2events 1 wins together · 1 podiums · 2 events · 12 of 52 races won Beat 58% of the fleet together · best 1st · Mar 2023 – Mar 2025

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

Rating history

-1074720020162018202020222024Helm rating, all classes

Event history · 36

DateEventBoatClassRoleFinish
5 Apr 2025Jeremy A. Pinkerton Memorial RegattaUniversity of Virginia (Wahoos)College fleet racingA Skipper2nd / 8
29 Mar 2025W&M Spring OpenUniversity of Virginia (Wahoos)College fleet racingB Skipper (3-6,9-10)1st / 9
19 Oct 2024Luce RegattaUniversity of Virginia (Wahoos)College fleet racingA Skipper5th / 15
20 Apr 2024America Trophy - Conference ChampionshipUniversity of Virginia (Wahoos)College fleet racingA Skipper18th / 18
6 Apr 2024Jeremy A. Pinkerton Memorial RegattaUniversity of Virginia (Wahoos)College fleet racingA Skipper (1-2,5)1st / 8
6 Jan 20242024 Rose Bowl RegattaUniversity of Virginia (Wahoos)College fleet racingA Skipper (1-2,5-6)14th / 16
11 Nov 20232023 Triangle Tango Intercollegiate RegattaUniversity of Virginia (Wahoos)College fleet racingA Crew8th / 10
9 Sep 2023Navy Women'sUniversity of Virginia (Wahoos)College fleet racingA Skipper8th / 9
29 Apr 2023America TrophyUniversity of Virginia (Wahoos)College fleet racingA Skipper (1-7)18th / 18
22 Apr 2023MAISA Women's Dinghy ChampionshipsUniversity of Virginia (Wahoos)College fleet racingA Skipper12th / 14
8 Apr 2023Jeremy A. Pinkerton Memorial RegattaUniversity of Virginia (Wahoos)College fleet racingA Skipper1st / 7
25 Mar 2023Hanbury TrophyUniversity of Virginia (Wahoos)College fleet racingB Skipper (1-2,5-6,9-10,13-14)12th / 14
29 Oct 2022MAISA Fall Women'sUniversity of Virginia (Wahoos)College fleet racingA Skipper10th / 11
15 Oct 2022Jefferson CupUniversity of Virginia (Wahoos 2)College fleet racingA Skipper (5-7)6th / 7
30 Jul 2021The C420 South Shore ChampionshipAnna Groszkowski420Skipper32nd / 64
20 Jul 20212021 Club 420 US National ChampionshipAnna Groszkowski420Skipper42nd / 132
14 Jul 20212021 C420 North American ChampionshipAnna Groszkowski420Skipper64th / 91
6 Jul 2021AYC Junior Annual8094420Skipper38th / 40
1 Jan 20212021 Sandy MacVickar Regatta8094420Skipper1st / 34
24 Oct 2020Halloween Howl8094420Skipper10th / 16
11 Aug 2020AYC Junior Annual8094420Skipper10th / 30
1 Aug 2020Oxford Regatta One Design - Optimist, Jr. 420 & Jr. Laser Radial8094420Skipper2nd / 16
18 Jul 20202020 Commonwealth of Virginia Championship8094420Skipper8th / 25
1 Jan 20202020 Sandy MacVickar8094420Skipper15th / 30
23 Jul 2019Annual Junior Regatta and Maryland State Championship8094Club 420 (spinnaker).Skipper18th / 18

Helm rating across all classes: 200, #18,626.Crew rating across all classes: 61. Compiled from public results; not an official ranking.