| Year | Single | Chart positions |
|---|
| US [10] [11] | US
R&B [12] | US
AC [13] | US Country | UK [14] |
|---|
| 1934 | "Two Cigarettes in the Dark" | 5 | — | — | — | — |
| "The Very Thought of You" | 11 | — | — | — | — |
| "The Moon Was Yellow" | 13 | — | — | — | — |
"June in January"
(from Crosbyana ) | 1 | — | — | — | — |
"Love Is Just Around the Corner"
(from Crosbyana ) | 8 | — | — | — | — |
"With Every Breath I Take"
(from Crosbyana ) | 4 | — | — | — | — |
| "Maybe I'm Wrong Again" | 14 | — | — | — | — |
| 1935 | "Soon"
(from Crosbyana ) | 1 | — | — | — | — |
"Down by the River"
(from Crosbyana ) | 17 | — | — | — | — |
"It's Easy to Remember"
(from Crosbyana ) | 1 | — | — | — | — |
"I Wished on the Moon"
(from Crosbyana ) | 2 | — | — | — | — |
"Without a Word of Warning"
(from Crosbyana ) | 5 | — | — | — | — |
"I Wish I Were Aladdin"
(from Crosbyana ) | 7 | — | — | — | — |
"From the Top of Your Head to the Tip of Your Toes"
(from Crosbyana ) | 10 | — | — | — | — |
| "Red Sails in the Sunset" | 1 | — | — | — | — |
"Silent Night" (gold record)
(from Christmas Music ) | 7 | — | — | — | — |
| "On Treasure Island" | 8 | — | — | — | — |
| 1936 | "Would You?" | 20 | — | — | — | — |
| "The Touch of Your Lips" | 4 | — | — | — | — |
| "Robins and Roses" | 2 | — | — | — | — |
| "It Ain't Necessarily So" | 18 | — | — | — | — |
"I'm an Old Cowhand"
(from Cowboy Songs ) | 2 | — | — | — | — |
| "I Can't Escape from You" | 7 | — | — | — | — |
"Empty Saddles"
(from Under Western Skies ) | 8 | — | — | — | — |
"Song of the Islands"
(from Music of Hawaii ) | 14 | — | — | — | — |
"South Sea Island Magic"
(from Favorite Hawaiian Songs ) | 3 | — | — | — | — |
| "Me and the Moon" | 9 | — | — | — | — |
| "Pennies from Heaven" | 1 | — | — | — | — |
| "Let's Call a Heart a Heart" | 10 | — | — | — | — |
| "So Do I" | 18 | — | — | — | — |
| 1937 | "One, Two, Button Your Shoe" | 19 | — | — | — | — |
"Sweet Leilani" (gold record)
(from Favorite Hawaiian Songs ) | 1 | — | — | — | — |
"Blue Hawaii"
(from Favorite Hawaiian Songs ) | 5 | — | — | — | — |
| "Too Marvelous for Words" | 1 | — | — | — | — |
| "What Will I Tell My Heart?" | 5 | — | — | — | — |
| "Sweet Is the Word for You" | 8 | — | — | — | — |
| "Never in a Million Years" | 2 | — | — | — | — |
| "Moonlight and Shadows" | 10 | — | — | — | — |
"My Little Buckaroo"
(from Cowboy Songs ) | 19 | — | — | — | — |
| "Peckin'" (w/ Jimmy Dorsey) | 9 | — | — | — | — |
| "The Moon Got in My Eyes" | 1 | — | — | — | — |
| "(You Know It All) Smarty" | 18 | — | — | — | — |
| "It's the Natural Thing to Do" | 2 | — | — | — | — |
| "Remember Me?" | 1 | — | — | — | — |
| "I Still Love to Kiss You Goodnight" | 6 | — | — | — | — |
| "Can I Forget You?" | 8 | — | — | — | — |
"Bob White (Whatcha Gonna Swing Tonight?)"
(w/ Connee Boswell) | 1 | — | — | — | — |
| "Basin Street Blues" (w/ Connee Boswell) | 12 | — | — | — | — |
| "The One Rose (That's Left in My Heart)" | 8 | — | — | — | — |
"Sail Along, Silv'ry Moon"
(from Favorite Hawaiian Songs ) | 4 | — | — | — | — |
| 1938 | "When the Organ Played 'O, Promise Me'" | 5 | — | — | — | — |
"There's a Gold Mine in the Sky" (w/ Eddie Dunstedter)
(from Cowboy Songs ) | 6 | — | — | — | — |
| "On the Sentimental Side" | 4 | — | — | — | — |
| "The Moon of Manakoora" | 10 | — | — | — | — |
| "Let Me Whisper I Love You" | 7 | — | — | — | — |
| "When Mother Nature Sings Her Lullaby" | 3 | — | — | — | — |
| "Now It Can Be Told" | 7 | — | — | — | — |
| "I've Got a Pocketful of Dreams" | 1 | — | — | — | — |
"Small Fry" (w/ Johnny Mercer)
(from Small Fry ) | 3 | — | — | — | — |
"Mr. Gallagher & Mr. Shean" (w/ Johnny Mercer)
(from Bing Crosby Sings with Judy Garland, Mary Martin, Johnny Mercer ) | 7 | — | — | — | — |
| "Alexander's Ragtime Band" (w/ Connee Boswell) | 1 | — | — | — | — |
| "Don't Let That Moon Get Away" | 19 | — | — | — | — |
"Mexicali Rose"
(from Cowboy Songs ) | 3 | — | — | — | — |
| "My Reverie" | 3 | — | — | — | — |
| "You Must Have Been a Beautiful Baby" | 1 | — | — | — | — |
| 1939 | "You're a Sweet Little Headache" | 3 | — | — | — | — |
| "I Have Eyes" | 4 | — | — | — | — |
| "The Funny Old Hills" | 5 | — | — | — | — |
| "Someone Stole Gabriel's Horn" (w/ The Dorsey Brothers) | 14 | — | — | — | — |
"It's a Lonely Trail"
(from Cowboy Songs ) | 17 | — | — | — | — |
"The Lonesome Road"
(from Star Dust ) | 12 | — | — | — | — |
"I Cried for You"
(from Star Dust ) | 13 | — | — | — | — |
| "Between a Kiss and a Sigh" | 15 | — | — | — | — |
"My Melancholy Baby"
(from Star Dust ) | 14 | — | — | — | — |
"Ah! Sweet Mystery of Life"
(from Victor Herbert Melodies, Vol. 1 ) | 12 | — | — | — | — |
| "East Side of Heaven" | 6 | — | — | — | — |
| "Sing a Song of Sunbeams" | 8 | — | — | — | — |
"Deep Purple"
(from Star Dust ) | 14 | — | — | — | — |
"God Bless America"
(from Patriotic Songs for Children ) | 17 | — | — | — | — |
"That Sly Old Gentleman (from Featherbed Lane)"
(from Small Fry ) | 10 | — | — | — | — |
"Little Sir Echo"
(from Small Fry ) | 3 | — | — | — | — |
| "And the Angels Sing" | 10 | — | — | — | — |
| "Alla en el rancho grande" | 6 | — | — | — | — |
| "Whistling in the Wildwood" | 14 | — | — | — | — |
"An Apple for the Teacher" (w/ Connee Boswell)
(from Small Fry ) | 2 | — | — | — | — |
| "Go Fly a Kite" | 10 | — | — | — | — |
| "A Man and His Dream" | 4 | — | — | — | — |
"Start the Day Right" (w/ Connee Boswell)
(from Bing and Connee) | 12 | — | — | — | — |
| "What's New?" | 2 | — | — | — | — |
"Ciribiribin (They're So in Love)" (w/ The Andrews Sisters)
(from Bing Crosby and The Andrews Sisters - EP) | 13 | — | — | — | — |
"Yodelin' Jive" (w/ The Andrews Sisters)
(from Bing Crosby and The Andrews Sisters - EP) | 4 | — | — | — | — |
"My Isle of Golden Dreams"
(from Favorite Hawaiian Songs ) | 18 | — | — | — | — |
| 1940 | "Between 18th & 19th on Chestnut Street" (w/ Connee Boswell)
(from Bing and Connee) | 12 | — | — | — | — |
| "Sweet Potato Piper" | 11 | — | — | — | — |
| "Just One More Chance" (re-recording) | 16 | — | — | — | — |
| "I'm Too Romantic" (aka "Too Romantic") | 3 | — | — | — | — |
"The Singing Hills"
(from Under Western Skies ) | 3 | — | — | — | — |
"Tumbling Tumbleweeds"
(from Under Western Skies ) | 12 | — | — | — | — |
| "April Played the Fiddle" | 10 | — | — | — | — |
| "I Haven't Time to Be a Millionaire" | 13 | — | — | — | — |
| "Meet the Sun Half-Way" | 15 | — | — | — | — |
"Sierra Sue"
(from Under Western Skies ) | 2 | — | — | — | — |
"Mister Meadowlark" (w/ Johnny Mercer)
(from Bing Crosby Sings with Judy Garland, Mary Martin, Johnny Mercer ) | 18 | — | — | — | — |
"Trade Winds"
(from Hawaii Calls ) | 2 | — | — | — | — |
| "Can't Get Indiana Off My Mind" | 8 | — | — | — | — |
| "That's for Me" | 9 | — | — | — | — |
| "Only Forever" | 1 | — | — | — | — |
| "When the Moon Comes Over Madison Square" | 27 | — | — | — | — |
"Where the Blue of the Night (Meets the Gold of the Day)" (re-recording)
(from Drifting and Dreaming ) | 27 | — | — | — | — |
| "You Made Me Love You" | 25 | — | — | — | — |
| 1941 | "Please" (re-recording) | 24 | — | — | — | — |
"Along the Santa Fe Trail"
(from Under Western Skies ) | 4 | — | — | — | — |
"Lone Star Trail"
(from Under Western Skies ) | 23 | — | — | — | — |
"New San Antonio Rose"
(from Don't Fence Me In ) | 7 | — | — | — | — |
"It Makes No Difference Now"
(from Don't Fence Me In ) | 23 | — | — | — | — |
"Did Your Mother Come From Ireland?"
(from St. Patrick's Day ) | 22 | — | — | — | — |
| "Dolores" | 2 | — | — | — | — |
"Paradise Isle"
(from Favorite Hawaiian Songs, Vol. One ) | 23 | — | — | — | — |
| "You and I" | 5 | — | — | — | — |
| "Brahms' Lullaby" | 20 | — | — | — | — |
| "'Til Reveille" | 6 | — | — | — | — |
"Be Honest With Me"
(from Don't Fence Me In ) | 19 | — | — | — | — |
"You Are My Sunshine"
(from Don't Fence Me In ) | 19 | — | — | — | — |
| "The Whistler's Mother-in-law" (w/ Muriel Lane) | 9 | — | — | — | — |
| "The Waiter and the Porter and the Upstairs Maid" (w/ Mary Martin & Jack Teagarden) | 23 | — | — | — | — |
| "Clementine" | 20 | — | — | — | — |
| "Shepherd Serenade" | 4 | — | — | — | — |
| "The Anniversary Waltz" | 24 | — | — | — | — |
| 1942 | "Deep in the Heart of Texas" | 3 | — | — | — | — |
| "I Don't Want to Walk Without You" | 9 | — | — | — | — |
"Sing Me a Song of the Islands"
(from Favorite Hawaiian Songs, Vol. Two ) | 22 | — | — | — | — |
| "Miss You" | 9 | — | — | — | — |
| "The Lamplighter's Serenade" | 23 | — | — | — | — |
| "When the White Azaleas Start Blooming" | 21 | — | — | — | — |
| "Skylark" | 14 | — | — | — | — |
| "The Bombardier Song" | 19 | — | — | — | — |
"Be Careful, It's My Heart"
(from Song Hits from Holiday Inn ) | 2 | — | — | — | — |
"White Christmas" (gold record)
(from Song Hits from Holiday Inn ) | 1 | 1 | 3 | — | 5 |
| "Moonlight Becomes You" | 3 | — | — | — | — |
| 1943 | "Constantly" | 13 | — | — | — | — |
| "Sunday, Monday, or Always" (gold record) | 1 | 3 | — | — | — |
| "If You Please" | 17 | — | — | — | — |
| "Mary's a Grand Old Name" | 20 | — | — | — | — |
"People Will Say We're in Love"
(from Bing Crosby Sings the Song Hits from Broadway Shows ) | 2 | — | — | — | — |
"Oh, What a Beautiful Mornin'"
(from Bing Crosby Sings the Song Hits from Broadway Shows ) | 4 | — | — | — | — |
"Pistol Packin' Mama" (w/ The Andrews Sisters)(gold record)
(from Don't Fence Me In ) | 2 | 3 | — | 1 | — |
| "Vict'ry Polka" (w/ The Andrews Sisters) | 5 | — | — | — | — |
"I'll Be Home for Christmas (If Only in My Dreams)" (gold record)
(from Merry Christmas ) | 3 | 8 | — | — | — |
| "White Christmas" (gold record) | 6 | — | — | — | — |
"Jingle Bells" (w/ The Andrews Sisters)
(from Merry Christmas ) | 19 | — | — | — | — |
"Let's Start the New Year Right"
(from Song Hits from Holiday Inn ) | 18 | — | — | — | — |
| 1944 | "San Fernando Valley" | 1 | — | — | — | — |
| "Poinciana" | 3 | — | — | — | — |
| "I Love You" | 1 | — | — | — | — |
| "I'll Be Seeing You" | 1 | — | — | — | — |
"Swinging on a Star" (gold record)
(from Selections from Going My Way ) | 1 | — | — | — | — |
"Going My Way"
(from Selections from Going My Way ) | 15 | — | — | — | — |
| "Is You Is or Is You Ain't My Baby" (w/ The Andrews Sisters) | 2 | — | — | — | — |
| "Amor" | 2 | — | — | — | — |
| "Long Ago (and Far Away)" | 5 | — | — | — | — |
| "The Day After Forever" | 15 | — | — | — | — |
| "Hot Time in the Town of Berlin" (w/ The Andrews Sisters) | 1 | — | — | — | — |
| "It Could Happen to You" | 18 | — | — | — | — |
"Too-Ra-Loo-Ra-Loo-Ral" (gold record)
(from Selections from Going My Way ) | 4 | — | — | — | — |
| "White Christmas" (gold record) | 5 | — | — | — | — |
"Don't Fence Me In" (w/ The Andrews Sisters)(gold record)
(from Don't Fence Me In ) | 1 | 9 | — | — | — |
| 1945 | "Evelina"
(from Bing Crosby Sings the Song Hits from Broadway Shows ) | 9 | — | — | — | — |
| "Ac-Cent-Tchu-Ate the Positive" (w/ The Andrews Sisters) | 2 | — | — | — | — |
| "The Three Caballeros" (w/ The Andrews Sisters) | 8 | — | — | — | — |
| "Sleigh Ride in July" | 14 | — | — | — | — |
| "Like Someone in Love" | 15 | — | — | — | — |
| "Just a Prayer Away" | 4 | — | — | — | — |
| "All of My Life" | 12 | — | — | — | — |
"Yah-ta-ta, Yah-ta-ta (Talk, Talk, Talk)" (w/ Judy Garland)
(from Bing Crosby Sings with Judy Garland, Mary Martin, Johnny Mercer ) | 5 | — | — | — | — |
"You Belong to My Heart"
(from El Bingo – A Collection of Latin American Favorites ) | 3 | — | — | — | — |
"Baia"
(from El Bingo – A Collection of Latin American Favorites ) | 6 | — | — | — | — |
| "My Baby Said Yes" (w/ Louis Jordan) | 14 | — | — | — | — |
| "On the Atchison, Topeka and the Santa Fe" | 3 | — | — | — | — |
"If I Loved You"
(from Bing Crosby Sings the Song Hits from Broadway Shows ) | 8 | — | — | — | — |
"Along the Navajo Trail" (w/ The Andrews Sisters)
(from Go West Young Man ) | 2 | — | — | — | — |
"It's Been a Long, Long Time" (w/ Les Paul Trio)
(from Drifting and Dreaming ) | 1 | — | — | — | — |
"The Road to Morocco" (w/ Bob Hope)
(from Selections from Road to Utopia ) | 21 | — | — | — | — |
| "I Can't Begin to Tell You" (gold record) | 1 | — | — | — | — |
| "White Christmas" (gold record) | 1 | — | — | — | — |
"Aren't You Glad You're You?"
(from Selections from The Bells of St. Mary's ) | 8 | — | — | — | — |
"In the Land of Beginning Again"
(from Selections from The Bells of St. Mary's ) | 18 | — | — | — | — |
| "Symphony" [15] | 3 | — | — | — | — |
| 1946 | "Give Me the Simple Life" | 16 | — | — | — | — |
"The Bells of St. Mary's"
(from Selections from The Bells of St. Mary's ) | 21 | — | — | — | — |
"McNamara's Band" (gold record)
(from St. Patrick's Day ) | 10 | — | — | — | — |
| "Day by Day" (w/ Mel Tormé & His Mel-Tones) | 15 | — | — | — | — |
| "Sioux City Sue" | 3 | — | — | — | — |
"Personality"
(from Selections from Road to Utopia ) | 9 | — | — | — | — |
"They Say It's Wonderful"
(from Bing Crosby Sings the Song Hits from Broadway Shows ) | 12 | — | — | — | — |
| "South America, Take It Away" (w/ The Andrews Sisters) [16] (gold record) | 2 | — | — | — | — |
| "(Get Your Kicks on) Route 66" (w/ The Andrews Sisters) | 14 | — | — | — | — |
| "Night and Day" | 21 | — | — | — | — |
"You Keep Coming Back Like a Song"
(from Blue Skies ) | 12 | — | — | — | — |
| "White Christmas" (gold record) | 1 | — | — | — | — |
| 1947 | "A Gal in Calico" | 8 | — | — | — | — |
"Easter Parade"
(from Song Hits from Holiday Inn ) | 22 | — | — | — | — |
| "That's How Much I Love You" | 17 | — | — | — | — |
"Alexander's Ragtime Band" (w/ Al Jolson)(gold record)
(from Bing Crosby Sings with Al Jolson, Bob Hope, Dick Haymes and the Andrews Sisters ) | 20 | — | — | — | — |
| "Tallahassee" (w/ The Andrews Sisters) | 10 | — | — | — | — |
"There's No Business Like Show Business" (w/ The Andrews Sisters & Dick Haymes)
(from Bing Crosby Sings with Al Jolson, Bob Hope, Dick Haymes and the Andrews Sisters ) | 25 | — | — | — | — |
"Feudin' and Fightin'"
(from Bing and the Dixieland Bands ) | 9 | — | — | — | — |
| "The Freedom Train" (w/ The Andrews Sisters) | 21 | — | — | — | — |
| "You Do" | 8 | — | — | — | — |
| "How Soon (Will I Be Seeing You)" | 6 | — | — | — | — |
"The Whiffenpoof Song" (gold record)
(from Auld Lang Syne ) | 7 | — | — | — | — |
| "White Christmas" (gold record) | 3 | — | — | — | — |
| "Santa Claus Is Comin' to Town" (w/ The Andrews Sisters) | 22 | — | — | — | — |
| "Silent Night" (new version) | 22 | — | — | — | 8 |
| 1948 | "Ballerina" | 10 | — | — | — | — |
"Now Is the Hour" (gold record)
(from Auld Lang Syne ) | 1 | — | — | — | — |
"You Don't Have to Know the Language" (w/ The Andrews Sisters)
(from Selections from Road to Rio ) | 21 | — | — | — | — |
| "Pass That Peace Pipe" | 21 | — | — | — | — |
"But Beautiful"
(from Selections from Road to Rio ) | 20 | — | — | — | — |
"Blue Shadows on the Trail"
(from Home on the Range) | 23 | — | — | — | — |
| "A Fella with an Umbrella" | 23 | — | — | — | — |
| "White Christmas" (gold record) | 6 | — | — | — | — |
"A Hundred and Sixty Acres" (w/ The Andrews Sisters)
(from Go West Young Man ) | 23 | — | — | — | — |
| 1949 | "Far Away Places" | 2 | — | — | — | — |
"Galway Bay" (gold record)
(from When Irish Eyes Are Smiling ) | 3 | — | — | — | — |
"If You Stub Your Toe on the Moon"
(from A Connecticut Yankee in King Arthur's Court ) | 27 | — | — | — | — |
| "Careless Hands" | 12 | — | — | — | — |
| "Riders in the Sky" | 14 | — | — | — | — |
"Some Enchanted Evening"
(from South Pacific ) | 3 | — | — | — | — |
"Bali Ha'i"
(from South Pacific ) | 12 | — | — | — | — |
| "Dear Hearts and Gentle People" (gold record) | 2 | — | — | — | — |
| "Mule Train" | 4 | — | — | — | — |
"Way Back Home"
(from Way Back Home ) | 21 | — | — | — | — |
| "White Christmas" (gold record) | 5 | — | — | — | — |
| 1950 | "Have I Told You Lately That I Love You?" (w/ The Andrews Sisters)
(from Go West Young Man ) | 24 | — | — | — | — |
"Quicksilver" (w/ The Andrews Sisters)
(from Go West Young Man ) | 6 | — | — | — | — |
| "Chattanoogie Shoe Shine Boy" | 4 | — | — | — | — |
| "I Didn't Slip, I Wasn't Pushed, I Fell" | 22 | — | — | — | — |
"Play a Simple Melody" (w/ Gary Crosby)(gold record)
(from Gary Crosby and Friend - EP) | 4 | — | — | — | — |
"Sam's Song" (w/ Gary Crosby)
(from Gary Crosby and Friend - EP) | 4 | — | — | — | — |
| "La Vie en rose" | 13 | — | — | — | — |
| "I Cross My Fingers" | 18 | — | — | — | — |
| "All My Love" | 11 | — | — | — | — |
| "Beyond the Reef" | 26 | — | — | — | — |
| "Harbor Lights" | 8 | — | — | — | — |
| "White Christmas" (gold record) | 13 | — | — | — | — |
| "Rudolph the Red-Nosed Reindeer" | 14 | — | — | — | — |
| "A Crosby Christmas" (w/ his sons) | 22 | — | — | — | — |
| 1951 | "A Marshmallow World" | 14 | — | — | — | — |
| "Sparrow in the Treetop" (w/ The Andrews Sisters) | 8 | — | — | — | — |
"When You and I Were Young, Maggie Blues" (w/ Gary Crosby)
(from Gary Crosby and Friend - EP) | 8 | — | — | — | — |
"Moonlight Bay" (w/ Gary Crosby)
(from Gary Crosby and Friend - EP) | 14 | — | — | — | — |
| "Gone Fishin'" (w/ Louis Armstrong) | 19 | — | — | — | — |
| "In the Cool, Cool, Cool of the Evening" (w/ Jane Wyman) | 11 | — | — | — | — |
| "Shanghai" | 21 | — | — | — | — |
| "Domino" | 15 | — | — | — | — |
| "White Christmas" (gold record) | 13 | — | — | — | — |
| 1952 | "The Isle of Innisfree"
(from Themes and Songs from The Quiet Man ) | — | — | — | — | 3 |
| "Watermelon Weather" (w/ Peggy Lee) | 28 | — | — | — | — |
| "Till the End of the World" | 16 | — | — | 10 | — |
"Zing a Little Zong" (w/ Jane Wyman)
(from Selections from the Paramount Picture "Just for You" ) | 18 | — | — | — | 10 |
| "Silver Bells" (w/ Carol Richards) | 20 | — | — | — | — |
| "Keep It a Secret" | 28 | — | — | — | — |
| 1953 | "You Don't Know What Lonesome Is"
(from Home on the Range) | 23 | — | — | — | — |
| "Open Up Your Heart" | 22 | — | — | — | — |
| "Hush-a-bye" | 24 | — | — | — | — |
| "White Christmas" (gold record) | 21 | — | — | — | — |
| 1954 | "Changing Partners"
(from Bing Sings the Hits ) | 13 | — | — | — | 9 |
"Y'all Come"
(from Bing Sings the Hits ) | 20 | — | — | — | — |
| "Down by the Riverside" (w/ Gary Crosby) | 28 | — | — | — | — |
| "Young at Heart" | 24 | — | — | — | — |
"Count Your Blessings Instead of Sheep"
(from Selections from Irving Berlin's White Christmas ) | 27 | — | — | — | 11 |
"White Christmas" (gold record)
(from Selections from Irving Berlin's White Christmas ) | 21 | — | — | — | — |
| 1955 | "Stranger in Paradise"
(from Bing Sings the Hits ) | — | — | — | — | 17 |
| "White Christmas" (gold record) | 7 | — | — | — | — |
| 1956 | "In a Little Spanish Town" (w/ Buddy Cole & his Trio)
(from In a Little Spanish Town) | 49 | — | — | — | 22 |
"True Love" (w/ Grace Kelly)
(from High Society ) | 3 | — | — | — | 4 |
"Well, Did You Evah!" (w/ Frank Sinatra)
(from High Society ) | 92 | — | — | — | — |
"Now You Has Jazz" (w/ Louis Armstrong)
(from High Society ) | 88 | — | — | — | — |
| "White Christmas" (gold record) | 65 | — | — | — | — |
| 1957 | "Around the World"
(from Around the World with Bing!) | 25 | — | — | — | 5 |
"How Lovely Is Christmas"
(from A Christmas Story – An Axe, an Apple and a Buckskin Jacket ) | 97 | — | — | — | — |
| "Silent Night" | 54 | — | — | — | — |
| "Silver Bells" (w/ Carol Richards) | 78 | — | — | — | — |
| "White Christmas" (gold record) | 34 | — | — | — | — |
| 1958 | 66 | — | — | — | — |
| 1959 | 59 | — | — | — | — |
| 1960 | "Adeste Fideles" | 45 | — | — | — | — |
| "I'll Be Home for Christmas (If Only in My Dreams)" (gold record) | 102 | — | — | — | — |
| "Silent Night" | 54 | — | — | — | — |
| "White Christmas" (gold record) | 26 | — | — | — | — |
| 1961 | 12 | — | — | — | — |
| 1962 | 38 | — | — | — | — |
| 1968 | "Step to the Rear" | — | — | 29 | — | — |
| 1975 | "That's What Life Is All About"
(from That's What Life Is All About ) | — | — | 35 | — | 41 |
| 1977 | "White Christmas" | — | — | — | — | 5 |
| 1982 | "Peace on Earth/Little Drummer Boy" (w/ David Bowie) | — | — | — | — | 3 |
| 1983 | "True Love" (w/ Grace Kelly) | — | — | — | — | 70 |
| 1985 | "White Christmas" | — | — | — | — | 69 |
| 1998 | — | — | — | — | 29 |
| 2018 | 34 | — | — | — | 61 |
| 2019 | 42 | — | — | — | 31 |
| 2020 | 20 | — | — | — | 49 |
| "Mele Kalikimaka (Merry Christmas)" (w/ The Andrews Sisters) | 36 | — | — | — | — |
| "I'll Be Home for Christmas (If Only in My Dreams)" | 50 | — | — | — | — |
| 2021 | "White Christmas" | 21 | — | — | — | 48 |
| 2022 | 16 | — | — | — | 39 |
| 2023 | 14 | — | — | — | 38 |
| 2024 | 32 | — | — | — | 66 |
