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Just select any of the contest below to get on the Triple M Guest List. Some contests require you to be a 105.5 Triple M Member.   If you're not a Member, sign up now.

Win Food & Drink at the Triple M Tailgate Party

Listen to Jonathan and Kitty in the Morning at 6:50a this week for a chance to win beverages and sandwiches or pizza for your and three buddies at the Rocky Rococo Tailgate on Regent this Saturday as Wisconsin takes on Bowling Green!

Party with Triple M two hours before each game at Rocky’s on Regent. Enjoy a cold beer from Potosi Brewing Company, the official beer of Triple M Tailgates. Rocky's also serves an extended menu of food starting with breakfast.

Quantity: 5 Gift Certificates
Value: $26
Winners daily on Jonathan & Kitty in the Morning 09.15-09.19

Win Tickets To Bras For A Cause

Listen to Jonathan and Kitty in the Morning at 8:40a for your chance to win a pair of tickets to the 4th Annual Bras For A Cause event, presented by the Women’s Council of Realtors will be held on Thursday, October 9th at the Madison Marriott West, starting at 5pm.

Quantity: 5 Pairs
Value: $70
Winners daily on Jonathan & Kitty in the Morning 09.15-09.19

Fall Into Tickets

It's a Fall Into Tickets weekend on 105.5 Triple M.  Text FALL to 20357 to enter to win tickets to these fall concerts: Pearl Jam, The 1975, Widespread Panic, Ryan Adams and Old Crow Medicine Show.  It's all presented by Potawatomi Hotel and Casino.

Value: $406.50
Enter before 9/22 for a chance to win

Get On The Triple M Guest List: John Mayer & Phillip Phillips

Text CHICAGO to 20357 for a chance to get on the Triple M Guest List to see John Mayer and Phillip Phillips at the Food Network In Concert show in at Highland Park in Chicago on Saturday, September 20th.   The winner will also receive overnight hotel stay in the Chicago area.

Value: $550
Enter before 9/20

Get On The Triple M Guest List: KONGOS

Listen to Stevi in the Radio Deli at 12:50 to win a pair of tickets to see KONGOS on Sunday, September 21 at Memorial Union Theater in Shannon Hall
AND $30 in Union Cab vouchers for Concert transportation!

Quantity: 5 Pairs
Value: $36
Winners daily in the Radio Deli 09.15-09.19

Free Ticket Thursday: Lorde

Listen for Lorde during Free Ticket Thursday (9.18) at 7am, 11am, 2pm & 5pm to win a pair of tickets to see Lorde in Milwaukee at the BMO Harris Pavilion on the Summerfest grounds on Friday, September 26 (7:30pm). 

Tickets & More Info Here

Quantity: 4 pairs
Value: $71
4 winners on Free Ticket Thursday 09.18

Free Ticket Friday: John Mellencamp

Free Ticket Friday Returns!  Listen at 7am, 11am, 2pm and 5pm on Friday, September 19th to win tickets to see John Mellencamp at Overture Hall on Tuesday, June 2nd.  Tickets go on sale Friday, September 19th.  More.

Concert Info

Value: TBA
Listen all day Friday, September 19th

Get On The Triple M Guest List: Brett Dennen

Listen to Jonathan & Kitty at 8:10am this week to win tickets to to see Brett Dennen on Wednesday, September 24 at Majestic Theatre. You'll also qualify to win Opera Box Seats and the Triple M VIP Concert Experience with an intimate acoustic pre-show performance, early entry to the show and a Meet & Greet with Brett Dennen. Concert information

Value: Grand Prize: $100, Tickets $50
Listen to Jonathan & Kitty In The Morning at 8:10am 9/14-9/19

Win $1,000,000 With The Million Dollar Vault

Enter for a chance to win $1,000,00 with the Million Dollar Vault.  Just Like us on Facebook and guess the correct vault combination to the Million Dollar Vault. 

Value: $1,000,000
Enter between 9/15 snd 9/26

Win Tickets To Once & A Romantic Dinner For 2

Text “ONCE” to 20357 to win a pair of tickets to ONCE on Tuesday, October 7th at Overture Hall, Overture Center for the Arts, plus a romantic dinner for two before the show at Brocach Pub and Restaurant on Capitol Square. Brocach will also provide drink tickets for the winning couple to use after the show, so they can enjoy open mic performances by local singer/songwriters.

Quantity: 1 Pair
Value: $200
Winners drawn on 09.29 and notified via text

See Derek Pritzl in Live From Studio M

Another exclusive chance to get on The Triple M Guest list to see an exclusive Live From Studio M performance.  Enter now to see Project M Finalist Derek Pritzl in Live From Studio M on Thursday, September 25th at Noon.  You and a guest will be invited to watch.

Value: Priceless
Enter before 9/23

See Delta Spirit In Live From Studio M

Get on the Triple M Guest List to see Delta Spirit in Live From Studio M on Wednesday, October 15th at Noon.  This is an exclusive chance to get up close and personal with this great Triple M artist.

Value: Priceless
Enter before 10/13

See Justin Townes Earle in Live From Studio M

Enter for your chance to get you and a friend on the Triple M Guest List to see Justin Townes Earle in Live From Studio M on September 24th at Noon!

Value: Priceless
Winners drawn on 09.22

Milio's Monday

It's Milio's Monday on the Radio Deli with Stevi every Monday at Noon!  Win a $50 gift card from Milio's Sandwiches!  Ready. Set. Order.

Quantity: 35 (1 per week)
Value: $50
Winner every Monday on the Radio Deli 05.05-12.29

Win a $50 Floral Arrangement From Metcalfe's Market

Metcalfe's Flowers at Work!  Enter to win a $50 floral arrangement, delivered to you at work from Metcalfe's Floral Studio. Just like Metcalfe's on Facebook and fill out a short form. We'll deliver the flowers to you!

Value: $50
Winners chosen weekly through 12/12/14

Win 4 Super Slice Combos From Rocky's

Listen to Jonathan & Kitty in the Morning at 6:50am for a chance to win lunch for you and THREE friends including Rocky’s Super slice pizza, Italian breadsticks (or 1-trip salad bar) and beverages. Earn more free pizza… join Rocky Rewards at

The latest Earth-Shattering news from Rocky Rococo's is that Meatzilla Pizzas are baaack!!

That's right – Meatzilla II at Rocky's features three pizzas loaded with massive mountains of meat; The Triple Sausage Spectacular, Fiery Buffalo Chicken, and The Meatzilla Meatworks are all specially priced at $15.99 for Large Pan Pizza – that's $4.00 Off!! Plus every week one
of these massive monsters of meat is available every day as a Super Slice Lunch Special.  So get on over to Rocky's for Meatzilla II Pizzas!!

Quantity: 5 per week (Contest runs Every Other Week beginning 03.24)
Value: $28
Winners daily during Jonathan & Kitty in the Morning every other week

Contest Rules

Click here to see general contest rules.

Texting Contests: Message & data rates may apply. Reply STOP to cancel. For Terms & Conditions and Privacy Policy please visit: Message frequency is recurring & varies.

Enter Your Text To Win Code Here

This is an entry form, in case you don't text or you're not into texting, but you still want to enter one of our texting contests.  Just enter the necessary contest info here:

Note: 105.5 Triple M's Short Code is 20357
The contest keyword is a contest specific word we provide.  (Example: Text MUSIC to 20357)

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