Hollywood Squares - Season 2

1. Santa's Got a Little Game

Aired: 12/22/2025

2. Hand This Man a Candy Cane

Aired: 12/22/2025

3. I Will Not Be Ignored, Glenn!

Aired: 1/7/2026

4. Between a Cardigan Sandwich

Aired: 1/7/2026

5. This Is the Best Show on TV

Aired: 1/14/2026

6. I'm Terrified of Triumph

Aired: 1/14/2026

7. Expect the Unexpected

Aired: 1/21/2026

8. This Always Happens When RuPaul’s Around

Aired: 1/21/2026

9. The Legacy Show

Aired: 1/28/2026

10. I Didn’t Know You Were That Flexible

Aired: 1/28/2026

11. Thicker Than a 1st Grade Pencil

Aired: 2/4/2026

12. I Have a Lot of Exes Watching Right Now

Aired: 2/4/2026

13. A Scream Reunion

Aired: 2/22/2026

14. I’m Nasty, But I Ain’t No Hero

Aired: 2/22/2026

15. This Isn’t Survivor

Aired: 3/11/2026

16. There’s That Cruella Energy

Aired: 3/18/2026

17. Please Don't Let It Be a Hawk

Aired: 3/25/2026

18. 90s Fine Baby

Aired: 4/8/2026

19. We Have a Lot of SNL Funny in Here Tonight

Aired: 4/15/2026

20. Be Careful What You Ask for Howie

Aired: 4/22/2026

Celebrities Whitney Cummings, Mark Duplass, Ana Gasteyer, Tiffany Haddish, Triumph the Insult Comic Dog, Leslie Jones, Thomas Lennon, Howie Mandel and Ross Mathews.

21. The Wizard of Hollywood Squares

Aired: 5/6/2026

Celebrities Michelle Buteau, Kat Dennings, Tiffany Haddish, Pete Holmes, Thomas Lennon, Bobby Moynihan, Law Roach and Meghan Trainor.

22. Snooze We Can't Lose

Aired: 5/27/2026

Celebrities Tom Bergeron, Neal Brennan, Whitney Cummings, Ariana DeBose, Mark Duplass, Arsenio Hall, Tiffany Haddish and Ms. Pat.