MassMutual Red Sox Grand Slam Sweepstakes

Posted Date: May 1, 2026

Win Green Monster seats for you and a guest to the Red Sox on 09/07/26 at Fenway Park, plus a signed jersey, meet-and-greet, and a Fenway Park tour.

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Prize Description:

2 winners get a pair of Green Monster seats for a Red Sox game at Fenway Park!

Prize also includes a player-signed jersey, a meet-and-greet, and a pre-game tour of Fenway Park!

144 winners will get other prizes like tickets to games, cleats, bats, a signed jersey, baseball, and hats!

Does not include travel.

Entry Frequency: Single Entry

Total Prizes: 146

Grand Prize ARV: $809

All Prizes ARV: $19,421

Start Date: April 3, 2026

End Date: September 30, 2026

Eligible States:
All states

All states

Quick Take!

Oh my gosh, Fenway dreams for the whole family, yes please. I love that this is a one-and-done entry, so it’s a quick win attempt that won’t clog up my inbox. Prize value is solid for a baseball fan, and it’s worth entering if you’d actually use tickets and a meet-and-greet. Skip it if you don’t live nearby or can’t cover travel and lodging.

How to Enter:

Online entry form

All Prizes

Grand Prize: (2 winners)

Two premium Green Monster seats for winner and one (1) guest to a Sponsor-specified Red Sox game on 09/07/26 at Fenway Park in Boston, MA
Sponsor-specified Red Sox player-signed jersey
Meet-and-greet with a Sponsor-specified Red Sox player (subject to availability)
Pre-game tour of Fenway Park

ARV: $809

Monthly Prize: (144 winners)

One (1) signed Green Monster Plate (ARV: $200)
Thirteen (13) signed jerseys (ARV: $224 each)
Four (4) signed baseball hats (ARV: $60 each)
Eighty-seven (87) signed baseballs (ARV: $30 each)
One (1) signed jacket (ARV: $250)
One (1) replica baseball glove (ARV: $550)
Two (2) replica pairs of cleats (ARV: $200 per pair)
Ten (10) signed baseball bats (ARV: $200 each)
Twenty-five (25) pairs of tickets to a Sponsor-specified baseball game (ARV: $212 – $378 per pair)

Total ARV: $18,612 (of all monthly prizes)

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Good to Know:

Limit one entry per person for the entire promotion; entries received by 07/31/26 are eligible for the Grand Prize; travel and lodging are not included; winners pay taxes.

Frequently Asked Questions:

Is this sweepstakes free to enter?

Yes it is. Entry is completely free and done online with no purchase required.

How and when will the winner be notified?

Potential Grand Prize winners will be notified via email and must sign and return Prize Documents within 48 hours; Monthly Prize winners will be notified via email and must verify eligibility and provide a mailing address within 48 hours.

Not sure what a real winner notification looks like? See real examples of actual sweepstakes winner emails on our How to Know If You Won page.

Is this sweepstakes legitimate?

Yes, this sweepstakes is run by Massachusetts Mutual Life Insurance Company and governed by the published official rules; the sponsor posts the rules and a winners list per the official rules.

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