| Date | Question | Answer | Winner Name | Hometown |
| 5/3 AM | What was Frank's favorite vodka? | Stolichnaya | Rich Krilich | Elmhurst, IL |
| | | | |
| 5/4 AM | What did Frank consider to be the perfect gentlemen's drink? | 2 fingers Jack Daniels, Water on the rocks in a traditional rocks glass | Anthony Piselli | Milford, CT |
| | | | |
| 5/4 PM | What was Frank's favorite color? | Orange | Aaron Minick | Nashville, TN |
| | | | |
| 5/5 AM | According to Frank, what color should men never wear after sundown? | Brown | Joel Zaremby | Norwlak, CT |
| | | | |
| 5/5 PM | According to Frank, what was the proper way to wear a hat? | 2 hands, back brim curled up and front tugged down a couple of inches above the right brow | Sam Guajardo | Ft. Worth, TX |
| | | | |
| 5/6 AM | What was the last solo recording Frank did and when?
| "Silent Night" August 27, 1991 | William Graham
| Medford, NJ
|
| | | | |
| 5/6 PM | What was the first song Frank recorded when he left the Tommy Dorsey Orchestra to work with Harry James and his Orchestra? | The question is reversed. Sinatra left James to work with Dorsey. | Tom Connolly, Jr. | Norwood. MA |
| | | | |
| 5/7 AM | What was the first song Frank recorded in stereo? | "Three Coins In The Fountain" 1954 | J. Sherry | Westbank, BC, Canada |
| | | | |
| 5/7 PM | Frank recorded two songs with Leonard Bernstein as conductor. Name one. | "Walking Down To Washington" or "The House I Live In" | Niclas Stilling | Stuttgart, Germany |
| | | | |
| 5/10 AM | What was the nickname for the portable bar the Rat Pack used on stage? | The Lunch Cart | Brenda Eggert | Lee's Summit, MO |
| | | | |
| 5/10 PM | What was Frank's first arrest number and when and where was he arrested? | #42799, Nov. 26/27, 1938, Bergen County Sheriff's Dept. Hackensak, NJ | Kris Cahill | West Ossipee, NH |
| | | | |
| 5/11 AM | According to Frank, what is the most offensive thing that can happen to a martini? | Warm vodka, there is nothing worse | Bryan Duff | Thousand Oaks, CA |
| | | | |
| 5/11 PM | According to Frank, what is the most dependable cure for a hangover? | Don't drink to begin with | Celia Wormley | London, ENG |
| | | | |
| 5/12 AM | In 1980, Frank made a resolution to give up drinking for one day. What day was it? | February 30th | Johnny V | Highland Lakes, NJ |
| | | | |
| 5/12 PM | On what date did Dean and Frank first appear at the Sands together? | January 28, 1959 | Kathy O'Leary | Farmington Hills, MI |
| | | | |
| 5/13 AM | According to Frank, what makes a perfect after-hours joint? | "A good piano player, good conversation, and people who like to stay up late. And some food helps too. | Bill Taggart | Richmond, VA |
| | | | |
| 5/13 PM | What were the last two songs Frank recorded with Harry James? | "Ciribiribin" and "Every Day of My Life" (Columbia - November 8, 1939) | Coy Sevier | Waxahachie, TX |
| | | | |
| 5/17 AM | When were the tracks from "Sinatra at The Sands with Count Basie and The Orchestra" recorded? | January 26th, 1966. At the Sands Hotel in Las Vegas, all songs arranged and conducted by Quincy Jones | Lance Johnson | Hutto, TX |
| | | | |
| 5/17 PM | What was Frank's favorite hat he ever wore? | The hat he wore in Pal Joey | Joe Hall | Riviera Beach, MD |
| | | | |
| 5/18 PM | Who was originally offered the role Frank won his Oscar for? | Eli Wallach was originally offered the role of Angelo Maggio but turned it down due to being offered the lead in Tennessee William's new play Camino Real. | Robert Scapparo | Middlevillage, NY |
| | | | |
| 5/19 AM | According to Frank, a shower is a great place to do what?
| Steam out the wrinkles in your dinner jacket | Doug Brashears | Camponello, SC |
| | | | |
| 5/21 PM | Columbia released Frank's first studio album on March 4th, 1946 - "The Voice of Frank Sinatra" - what's special about that album - besides it's his first? | It's the first pop LP to be released playing HiFi at 33 1/3 rpm. | Eric Jallo | Glendora, CA |
| | | | |
| 5/24 AM | According to Frank, what should a man never do in the presence of a woman? | Yawn | Phyllis C. Mendenhall | Elk Grove, CA |
| | | | |
| 5/24 PM | Which building is lit up with blue lights each year for Frank's birthday? | The Empire State Building | Noelle Shell | West Covina,CA |
| | | | |
| 5/25 AM | Frank Sinatra was the Grand Marshal of a very famous parade. What parade was it and what was the date of the parade? | Tournament of Roses Parade - Jan. 1, 1980 | Joe Lang | Elmwood Park, IL |
| | | | |
| 5/25 PM | According to Frank, how do you know when a hat looks right on you? | When no one laughs | Vicky Denison
| Southfield, MI |
| | | | |
| 5/26 AM | Two weeks after JFK was shot, Frank Sinatra, Jr. was kidnapped. How high was the ransom | $240,000 | Sherif Lepi | Albquerque, NM |
| | | | |
| 5/27 PM | What alcohol related act was considered a sign of friendship from Frank? | He always shared an olive from his martini. | Deana Pendragon | Charlotte, NC |
| | | | |
| | | | |