My Review: VIP Experience | Bailey Zimmerman Concert with Ninety9 Entertainment and BET99

Smiling in the VIP North Floor Box at HISTORY Toronto in a fun country glam dress for the BET99 Bailey Zimmerman concert experience!

I love live music, but I think my favorite concert genre is "having a private bar + private spotless bathroom and zero line ups" 🤠✨

When Ninety9 Entertainment and BET99 invited me to see country superstar Bailey Zimmerman live at HISTORY Toronto for 'Same Night Different Rodeo,' I was beyond excited.

This event was actually the very first of a new series where they are bringing massive, stadium-level artists into stunningly intimate venues. Being there for the launch of this series was an absolute dream!

​Here is an inside look at my country glam aesthetic, the white-glove hospitality, and why this is the only way you will want to experience live music from now on.

Full body outfit photo wearing a black cowboy hat, fringe boots, and a burgundy maxi dress in a modern hallway at HISTORY Toronto! 🤍

​The Look: Elevated Country

​Getting dressed for a country show in the city requires a very specific balance.

I gravitated toward a burgundy cut-out maxi dress with velvet floral burnout details from Zara. I originally had a two piece halter pants set, but did a last minute swap for this dress instead.

I added a black cowboy hat, layered silver chains, and black fringe boots with silver hardware - from Amazon Fashion.

Throwing on a statement coat with pink trim (from Asos) pulled the entire vibe together.

Super comfy and completely on-theme.

--

Dress :

Zara - ASYMMETRIC FLOCKED TULLE CUT OUT DRESS | I'm normally a size S, but wore a size M.

Dark burgundy | 1131/312/684

Why the VIP Upgrade is the Ultimate Hack ✨

HISTORY is already one of Toronto's premier venues, but experiencing it through the lens of Ninety9 Entertainment and BET99 was a completely elevated experience.

If you are ever debating treating yourself to a VIP upgrade for your next concert, here is exactly why it is worth every single penny:

  • Zero Line Anxiety: We walked right past the massive crowd outside and went straight through a private entry. There was comped coat check :).

  • Room to Breathe: The North Floor Box gave us a totally unobstructed, premium view of the stage. We actually had space to dance & sing without spilling our drinks on anyone. There was comfy seating area as well!

  • A Dedicated Custom Bar: Instead of missing songs to wait in line at the bar, we had a private bar featuring a customized VIP drinks menu right in our section! We had our pick of wine and classic cocktails like Aperol Spritzes and Cosmopolitans. I was sipping on my absolute favorite Spicy Guavarita, along with a clever specialty drink called The 6ixth Borough🍹. I ended the evening with a glass of prosecco.

  • The Holy Grail: And the ultimate luxury for any girls night out? A spotless, private bathroom with absolutely zero wait time. Honestly, this alone is the greatest luxury of adulthood when you just want to get back to the music 🥺!

Courtney and I smiling with cocktails in our private VIP booth with the concert stage glowing behind us during our Toronto girls night!
Fun country glam outfit! Pointing at the Bailey Zimmerman tour marquee outside HISTORY Toronto, skipping the massive general line. ✨

Redefining the Fan Experience

If you thought BET99 was only a premiere online casino and sportsbook, you are totally missing out! They are now also the number one Canadian platform for elite fan experiences.

They know exactly how to throw a party and bring fans closer to the artists they love.

Partnering with Ninety9 Entertainment to create these intimate concert moments is so brilliant.

You have to check out all the amazing things they are doing next at ninety9entertainment.com and bet99.com!

Unobstructed VIP view of Bailey Zimmerman performing live on stage at HISTORY Toronto for his Different Night Same Rodeo Tour. 🤠

The Verdict

​Bailey Zimmerman’s live vocals are out of this world. The crowd was electric, the hospitality was incredible, and the entire night was a nothing short of spectacular. Would I do it again? A million times YES.

ninety9entertainment.com

bet99.com

Bailey Zimmerman Toronto 2026, HISTORY Toronto concert review, Different Night Same Rodeo Tour setlist, VIP concert experience Toronto, Ninety9 Entertainment, BET99 Canada, Toronto girls night out, country concert outfit ideas, Hudson Westbrook, Blake Whiten, The Climb cover live.