| 1944 | Small Fry / Forget‐Me‐Nots in Your Eyes | Bing Crosby with Tommy Dorsey and His Orchestra / Perry Como | | 1 |
| 1944 | Don’t Fence Me In / The Three Caballeros | Bing Crosby and The Andrews Sisters with Vic Schoen and His Orchestra | | 1 |
| 1944 | Is You Is or Is You Ain’t (Ma’ Baby) / (There’ll be a) Hot Time in the Town of Berlin (When the Yanks Go Marching In) | Bing Crosby and The Andrews Sisters with Vic Schoen and His Orchestra | | 1 |
| 1944 | Poinciana (Song of the Tree) / San Fernando Valley | Bing Crosby with John Scott Trotter and His Orchestra | | 1 |
| 1944 | Too‐Ra‐Loo‐Ra‐Loo‐Ral (That’s an Irish Lullaby) / I’ll Remember April | Bing Crosby with John Scott Trotter and His Orchestra | | 1 |
| 1944 | The Day After Forever / It Could Happen to You | Bing Crosby with John Scott Trotter and His Orchestra | | 1 |
| 1945 | On the Atchison, Topeka and the Santa Fe / I’d Rather Be Me | Bing Crosby with Six Hits and a Miss and John Scott Trotter and His Orchestra | | 1 |
| 1945 | Good, Good, Good (That’s You–That’s You) / Along the Navajo Trail | Bing Crosby and The Andrews Sisters with Vic Schoen and His Orchestra | | 1 |
| 1945 | Give Me the Simple Life / Dearly Beloved | Bing Crosby with Jimmy Dorsey and His Orchestra / Bing Crosby with John Scott Trotter and His Orchestra | | 1 |
| 1945 | Symphony / Beautiful Love | Bing Crosby | | 1 |
| 1945 | Along the Navajo Trail / I Can’t Believe That You’re in Love With Me | Bing Crosby & The Andrews Sisters with Orchestra Under Direction of Vic Schoen / Bing Crosby with Carmen Cavallaro | | 1 |
| 1945 | It’s Been a Long Long Time / Whose Dream Are You | Bing Crosby with Les Paul and His Trio | | 1 |
| 1945 | I Can’t Begin to Tell You / I Can’t Believe That You’re in Love With Me | Bing Crosby with Carmen Cavallaro | | 1 |
| 1945 | Just a Prayer Away / My Mother’s Waltz | Bing Crosby with Ken Darby Singers, Ethel Smith & Victor Young and His Orchestra | | 1 |
| 1945 | The Bells of St. Mary’s / I’ll Take You Home Again, Kathleen | Bing Crosby with John Scott Trotter and His Orchestra | | 1 |
| 1945 | You Belong to My Heart / Baía | Bing Crosby and Xavier Cugat and His Orchestra | | 1 |
| 1946 | Medley From “Dixie” | Bing Crosby and Risé Stevens with John Scott Trotter and His Orchestra / Bing Crosby with The Charioteers and John Scott Trotter and His Orchestra | | 1 |
| 1946 | South America, Take It Away / Get Your Kicks on “Route 66!—” | Bing Crosby and The Andrews Sisters with Vic Schoen and His Orchestra | | 1 |
| 1946 | The Things We Did Last Summer / Sweet Lorraine | Bing Crosby and Jimmy Dorsey and His Orchestra | | 2 |
| 1946 | Yours Is My Heart Alone / The Anniversary Waltz | Bing Crosby with John Scott Trotter and His Orchestra / Bing Crosby with Victor Young and His Orchestra | | 1 |
| 1946 | Give Me the Simple Life / It’s the Talk of the Town | Bing Crosby and Jimmy Dorsey and His Orchestra | | 1 |
| 1947 | Too‐Ra‐Loo‐Ra‐Loo‐Ral (That’s an Irish Lullaby) / I’ll Take You Home Again, Kathleen | Bing Crosby with John Scott Trotter and His Orchestra | | 1 |
| 1947 | Alexander’s Ragtime Band / The Spaniard That Blighted My Life | Bing Crosby and Al Jolson with orchestra directed by Morris Stoloff | | 1 |
| 1947 | Whiffenpoof Song / Kentucky Babe | Bing Crosby with Fred Waring and the Glee Club | | 1 |
| 1947 | Too Marvelous for Words / Wrap Your Troubles in Dreams (and Dream Your Troubles Away) | Bing Crosby and Jimmy Dorsey and His Orchestra / Bing Crosby and John Scott Trotter and His Orchestra | | 1 |
| 1947 | Now Is the Hour (Maori Farewell Song) / Silver Threads Among the Gold | Bing Crosby with Ken Darby Choir | | 1 |
| 1947 | White Christmas / God Rest Ye Merry Gentlemen | Bing Crosby with Ken Darby Choir and John Scott Trotter and His Orchestra | | 1 |
| 1948 | Far Away Places / Tarra Ta‐Lara Ta‐Lar | Bing Crosby with Ken Darby Choir | | 1 |
| 1948 | Sweet Leilani / Aloha Oe (Farewell to Thee) | Bing Crosby with Lani McIntire and His Hawaiians / Bing Crosby with Dick McIntire and His Harmony Hawaiians | | 1 |
| 1949 | Mule Train / Dear Hearts and Gentle People | Bing Crosby with Perry Botkin’s String Band | | 1 |
| 1950 | Play a Simple Melody / Sam’s Song (The Happy Tune) | Gary Crosby and Friend with Matty Matlock’s All Stars | | 1 |
| 1950 | A Marshmallow World / Looks Like a Cold, Cold Winter | Bing Crosby with Lee Gordon Singers and Sonny Burke and His Orchestra | | 1 |
| 1950 | Here Comes Santa Claus (Right Down Santa Claus Lane) / Twelve Days of Christmas (Traditional Christmas Carol) | Bing Crosby and The Andrews Sisters with Vic Schoen And His Orchestra | | 1 |
| 1950 | I Didn't Slip, I Wasn't Pushed, I Fell | Bing Crosby with Sy Oliver and His Orchestra | | 3 |
| 1950 | La Vie en rose / I Cross My Fingers | Bing Crosby with orchestra directed by Axel Stordahl | | 1 |
| 1950 | Poppa Santa Claus / Mele Kalikimaka | Bing Crosby and Andrews Sisters with Vic Schoen and His Orchestra | | 2 |
| 1950 | Rudolph the Red‐Nosed Reindeer / The Teddy Bears’ Picnic | Bing Crosby | | 1 |
| 1950 | Side by Side / Magnolia | Bing Crosby and The Rhythm Boys with Paul Whiteman’s Orch. | | 1 |
| 1950 | That Christmas Feeling / Silver Bells | Bing Crosby with Jeff Alexander Chorus and John Scott Trotter and His Orchestra / Bing Crosby and Carol Richards with John Scott Trotter and His Orchestra | | 2 |
| 1951 | Alexander's Ragtime Band / The Spaniard That Blighted My Life / The Old Piano Roll Blues / 'Way Down Yonder In New Orleans | Al Jolson - The Andrews Sisters - Bing Crosby | | 1 |
| 1951 | Christmas in Killarney / It’s Beginning to Look a Lot Like Christmas | Bing Crosby with Jud Conlon’s Rhythmaires and John Scott Trotter and His Orchestra | | 1 |
| 1951 | Gone Fishin’ / We All Have a Song in Our Heart | Bing Crosby and Louis Armstrong with John Scott Trotter and His Orchestra / Bing Crosby with Lyn Murray and His Orchestra | | 1 |
| 1951 | In the Cool, Cool, Cool of the Evening (from Paramount picture “Here Comes the Groom”) / Misto Cristofo Columbo (from Paramount picture “Here Comes the Groom”) | Bing Crosby and Jane Wyman with The 4 Hits and a Miss and Matty Matlock’s All Stars | | 1 |
| 1951 | The Girl Friend / Without a Word of Warning | Bing Crosby, Tommy Dorsey and His Orchestra | | 2 |
| 1952 | Sleigh Ride / Little Jack Frost Get Lost | Bing Crosby with Jud Conlon’s Rhythmaires / Bing Crosby and Peggy Lee | | 1 |
| 1954 | Young at Heart / (Oh Baby Mine) I Get So Lonely | Bing Crosby and Guy Lombardo And His Royal Canadians | | 1 |
| 1954 | Y’all Come / Changing Partners | Bing Crosby | | 1 |
| 1956 | True Love / Well Did You Evah? | Bing Crosby | | 2 |
| 1956 | I Heard the Bells on Christmas Day/ Christmas Is A-Comin' (May God Bless You) | Bing Crosby | | 1 |
| 1957 | I'm Gonna Sit Right Down and Write Myself a Letter / Last Night on the Back Porch | Bing Crosby With Bob Scobey's Frisco Band | | 1 |
| 1958 | It's Beginning to Look Like Christmas | Bing Crosby | | 1 |
| 1959 | Never Be Afraid | Bing Crosby | | 1 |
| 1963 | Do You Hear What I Hear? / Christmas Dinner Country Style | Bing Crosby | | 1 |
| 1970 | White Christmas / Jingle Bells | Bing Crosby | | 1 |
| 1977 | White Christmas | Bing Crosby | | 2 |
| 1977 | Peace on Earth / Little Drummer Boy | David Bowie & Bing Crosby | | 7 |
| 1997 | Little Drummer Boy (Peace on Earth) | Bing Crosby & David Bowie | | 1 |
| 2012 | White Christmas | Michael Bublé and Bing Crosby | | 1 |
