2nd Annual · Official Event Site
Boston’s nursery-school dads settle it on the pickleball court and the cornhole boards — for the kids, organized by the dads, with a cash prize for the winning school(s).
PLAYERS + SPECTATORS · T-SHIRT SIZE COLLECTED AT SIGN-UP · @SIPPYCUPINVITATIONAL
Date, venue, and how to join — everything a player, a spectator, or a sponsor needs, in one place.
4:00–7:00 PM
Saturday, November 14, 2026. After nap time, before bedtime.
64 C St, South Boston — the Iron Works building. Indoor courts, boards, and a bar. Street parking nearby is limited on a Saturday; arrive early or rideshare. Get directions →
Two disciplines. One overall champion crowned at PKL at the end of the night.
Represent your school, play for the cup, and take home bragging rights for a full calendar year.
A spot on one of your school’s pickleball teams. Player tickets include swag.
Compete on the boards all night. Player tickets include swag.
Full access to the room, the finals, and the heckling.
Every ticket includes admission, open bar, food, and shenanigans.
You don’t have to be good at both. You do have to pick a school and commit — no super teams.
Doubles play at PKL Boston. Fast, loud, and significantly more athletic than anyone’s current lifestyle strictly supports.
The great equalizer. Lower vertical, higher heckling ceiling. Where the tournament is actually won and lost.
FORMAT NOTE — PICKLEBALL AND CORNHOLE RESULTS COMBINE INTO ONE OVERALL CHAMPION. THE COMMITTEE IS FINALIZING SCORING, PARTNER PAIRING, ELIGIBILITY, AND THE PRIZE SPLIT; FINAL RULES WILL BE POSTED HERE AHEAD OF THE EVENT.
Six Boston schools, one cup. Every school plays both sports, and every dad plays for the school his family calls home.
Back Bay’s entry, back for year two and playing for the cup again.
First to send its save-the-date, and already reporting more sign-ups than last year — and defending the Cup it won in year one.
New to the field for 2026 — the year-two addition, joining after the inaugural tournament, with dads on the rules committee as well as the courts.
New to the field this year after sitting out the inaugural tournament.
In the field from day one — a year-one original back for year two. Knight logo, full squad, no shortcuts.
Where the Croft families landed — “the school formerly known as Croft.” They bring the bags pedigree with them: Croft took two cornhole semifinal berths and finished third overall in year one.
New schools are welcome to join the field. Eligibility details are being confirmed by the committee — reach out through the sign-up form and we’ll get you in the loop.
CHANGES FROM YEAR ONE — THE INAUGURAL FIELD WAS FIVE SCHOOLS: SPRUCE, JWS, CROFT, KINGSLEY AND PARK STREET (THE FIVE HATS UP TOP). LAST YEAR’S RUNNER-UP, JWS, AND THIRD-PLACE CROFT AREN’T FIELDING TEAMS IN 2026 — CROFT’S FAMILIES ARE NOW AT SEVA. ADVENT, BEACON HILL AND SEVA JOIN THE FIELD.
November 15, 2025. More than 80 people came out for the inaugural tournament — a night of competition, drinks, and good fun all around. Congratulations to the first-ever Sippy Cup champion: Spruce. And to the runner-up, JWS — by two controversial points.
When the clock hit 4:35 PM, 16 pickleball teams kicked off blistering round-robin play. Paddles swung, balls flew, and when the dust settled, four teams advanced to the semifinals — three of them from JWS. The captains had foreseen exactly this: a school could send only two teams to the semifinals, and only one to the final. That bumped the fifth-best team into a semifinal berth — which is when the Spruce contingent burst into the tournament control room and demanded a recount, dripping sweat onto the commissioner’s keyboard.
The review found a genuine error in the scoring spreadsheet (what’s an absolute cell reference amongst friends?). Corrected, Spruce took the semifinal berth at JWS’s expense. Spruce beat Kingsley in the semi — self-directed Montessori learning doesn’t make for great defense — then assembled a super-team of its best players for the final, a move the 2025 rulebook didn’t address. It does now. After a hard-fought final, Spruce, which had won just two paltry games in round-robin play, was crowned pickleball champion and earned 14 tournament points. But the Cup wasn’t theirs yet: cornhole was still to come, and with it the points that would decide the night.
The cornhole competition was a little less… fierce. There was much shouting back to the bar of “Dude! Get over here, our game is starting!” Croft emerged as the dominant bags school of the night, taking two semifinal berths — the South End crew apparently knows how to throw a bag. Spruce took down Croft’s #2 team, and JWS narrowly fell to Croft #1, 15–13.
With pickleball decided, JWS needed a third-place cornhole finish to tie Spruce for the tournament lead. Instead, Spruce unleashed their New Orleans “Bayou B2,” who dropped precision-guided bombs throw after throw and laid waste to JWS’s dreams of glory. Spruce’s cornhole finish added 14 more points to the 14 from pickleball — 28 in all, two clear of JWS, with Croft third on 20.
Thank you to everyone who came out and made year one a huge success. The Sippy Cup returns November 14, 2026 — and this time, the super-team loophole is closed.
Three hours. That’s the whole commitment — doors at 4, champion crowned by 7, home before anyone’s bedtime routine fully collapses.
Find your school, find your partner, and get a few rallies in before the matches count.
Pickleball and cornhole run side by side. Every match moves your school closer to the cup — and the cash prize.
Championship matches in both sports. Spectators: this is your moment too.
Overall champion crowned at PKL. The winning school(s) take the cash prize, the cup, and bragging rights until next November.
An event for the entire school community, planned by dads — with committee chairs and an independent audit committee looking after the money.
Founded the tournament, runs the meetings, and audits the spreadsheets. Especially the spreadsheets.
Runs the sign-up form and leads sponsor outreach to local businesses.
Venue, food, and beverages with PKL Boston. The contact on the Kingsley flyer — playing for Kingsley? He’s your email.
Works across the schools to keep the field together.
The Sippy Cup puts a local business in front of Boston nursery-school families from six schools — players, partners, and spectators, all in one room on a Saturday night, plus the parents who hear about it for the rest of the school year. More than 80 people turned out for year one.
Dads competing for six Boston nursery schools, with spectators welcome from the whole school community. More than 80 people turned out for the inaugural tournament in 2025, and Spruce is already reporting more sign-ups than last year. Year one was backed by local sponsors and school families; confirmed 2026 sponsors will be named here.
Sponsorships help cover the courts and the cash prize for the winning school(s) — and put your name on the night.
Interested in sponsoring? Email bostonsippycup@gmail.com, find us at @sippycupinvitational, or ask your school’s committee contact.
The practical stuff — cost, deadlines, and rules included. Anything still marked to be confirmed gets posted here the moment the committee locks it in.
Dads from the six participating schools. Alumni eligibility is being finalized by the committee and will be in the final rules posted here ahead of the event. One house rule is already settled: no alumni over 6 feet.
Pickleball player $225, cornhole player $175, spectator $125. Every ticket includes admission, open bar, food, and shenanigans; player tickets include swag.
The deadline is to be confirmed — it’s set by t-shirt orders and the number of courts we reserve at PKL, so sooner is better. The confirmed date will be posted here and on @sippycupinvitational.
Pickleball is doubles. Whether you register with a partner or get paired on the night is part of the final format — scoring, pairing, and the prize split will be posted here ahead of the event.
Yes — spectators are welcome and encouraged. This is an event for the entire school community: there’s a bar, two finals to watch, and championship-level heckling.
Find a babysitter. That’s straight from the flyer. It’s for the kids — the event, that is. The evening itself is grown-ups only.
This is dads running a tournament that also raises funds. Schools compete, and the winning school(s) receive a cash prize; an independent audit committee looks after the money.
PKL Boston is at 64 C St in South Boston, in the Iron Works building. Street parking nearby is limited on a Saturday — arrive early, or rideshare and skip the circling.
Use the sign-up form — it collects your school and t-shirt size. Kingsley dads can also email Jamie, per the school flyer.
New schools are welcome. Eligibility details are being confirmed by the committee — reach out through the sign-up form and we’ll follow up.
Spruce already has more sign-ups than last year. Your school’s honor is, at this point, a sign-up-form problem. Players and spectators both register — it takes a minute, and yes, there’s a t-shirt size field.
Tickets: pickleball $225 · cornhole $175 · spectator $125 — includes open bar, food & swag for players · sign-up deadline to be confirmed
Questions? bostonsippycup@gmail.com · @sippycupinvitational
SAT NOV 14, 2026 · 4:00–7:00 PM · PKL BOSTON, 64 C ST, SOUTH BOSTON · SPECTATORS WELCOME · FIND A BABYSITTER