| 1925 | I'm Gonna Cry / Nights When I Am Lonely | Connie Boswell / Boswell Sisters | | 1 |
| 1931 | Stardust / Concentratin’ | Bing Crosby / Connie Boswell | | 1 |
| 1931 | You Try Somebody Else / Should I Be Sorry? | Connie Boswell | | 1 |
| 1932 | Lullaby of the Leaves / My Lips Want Kisses (My Heart Wants Love) | Connee Boswell | | 1 |
| 1932 | Say It Isn't So / Where I Wonder Where | Connie Boswell | | 1 |
| 1932 | I Cried for You / I Can't Believe That It's You | Connie Boswell | | 1 |
| 1932 | Washboard Blues / Four Indian Love Lyrics | Casa Loma Orchestra with Connie Boswell | | 1 |
| 1933 | It's All My Fault / Time on My Hands | Connie Boswell | | 1 |
| 1934 | Lost in a Fog / Isn't It a Shame? | Connie Boswell With Jimmie Grier & His Orchestra | | 1 |
| 1934 | It's the Talk of the Town / This Time It's Love | Connie Boswell | | 1 |
| 1935 | Clouds / Blue Moon | The Boswell Sisters / Connee Boswell | | 1 |
| 1935 | I Can't Give You Anything but Love / Life Is a Song | Connie Boswell | | 1 |
| 1935 | With Every Breath I Take / I'm Growing Fonder of You | Connie Boswell | | 1 |
| 1935 | You Are My Lucky Star / I've Got a Feelin' You're Foolin' | Connie Boswell | | 2 |
| 1936 | Moon Over Miami / With All My Heart | Connie Boswell | | 2 |
| 1936 | Blue Moon / You're All I Need | Connie Boswell | | 1 |
| 1936 | On the Beach at Bali Bali / I Met My Waterloo (Down by the Beautiful Sea) | Connie Boswell | | 1 |
| 1936 | Swing Me a Lullaby / You Can Call It Swing | Connie Boswell | | 2 |
| 1936 | Seein' Is Believin' / Chasing Shadows | Connie Boswell | | 1 |
| 1936 | The Panic Is On / Mama Don't Allow It | Connie Boswell | | 1 |
| 1936 | Things Might Have Been So Different / I'll Never Say "Never Again" Again | Connie Boswell | | 1 |
| 1936 | You Started Me Dreaming / Mommy | Connie Boswell With Bob Crosby & His Orchestra | | 2 |
| 1937 | When the Poppies Bloom Again / Trust in Me | Connie Boswell With Ben Pollack And His Orchestra | | 2 |
| 1937 | Basin Street Blues / Bob White (Whatcha Gonna Swing Tonight?) | Bing Crosby and Connie Boswell with John Scott Trotter and His Orchestra | 5 | 7 |
| 1937 | Afraid to Dream / The Loveliness of You | Connie Boswell | | 1 |
| 1937 | Blossoms on Broadway / Love or Infatuation | Connie Boswell With Ben Pollack And His Orchestra | | 1 |
| 1937 | Serenade in the Night / Where Are You? | Connie Boswell With Ben Pollack And His Orchestra | | 2 |
| 1937 | That Old Feeling / Yours and Mine | Connie Boswell With Ben Pollack And His Orchestra | | 1 |
| 1937 | Whispers in the Dark / That Old Feeling | Connie Boswell With Ben Pollack And His Orchestra | | 1 |
| 1937 | Where Are You? / Trust in Me | Connie Boswell | | 2 |
| 1937 | Yours and Mine / Am I in Love? | Connie Boswell With Ben Pollack And His Orchestra | | 1 |
| 1938 | All Alone / Remember | Connie Boswell With Harry Sosnik And His Orchestra | | 2 |
| 1938 | Gypsy Love Song / Ah! Sweet Mystery of Life | Connie Boswell With Bob Crosby's Bob Cats | | 3 |
| 1938 | Martha / Home on the Range | Connie Boswell With Bob Crosby's Bob Cats | | 3 |
| 1938 | Mr. Freddie Blues / Fare Thee Honey Fare Thee Well | Connie Boswell With Ben Pollack And His Pick-A-Rib Boys | | 1 |
| 1938 | Simple and Sweet / Heart and Soul | Connie Boswell | | 1 |
| 1938 | True Confession / Ebb Tide | Connie Boswell | | 4 |
| 1938 | There's Something About an Old Love / Heart and Soul | Connie Boswell | | 1 |
| 1938 | There's Something About an Old Love / Summer Souvenirs | Connie Boswell | | 1 |
| 1938 | You Took the Words Right Out of My Heart / Outside of Paradise | Connie Boswell | | 2 |
| 1938 | You Leave Me Breathless / If It Rains-Who Cares! | Connie Boswell | | 2 |
| 1938 | You're the Only Star (In My Blue Heaven) / When Christmas Is Gone | Connie Boswell With The Lyn Murray Singers | | 1 |
| 1939 | Thanks for Ev’rything / Deep in a Dream | Connie Boswell with Woody Herman and His Orchestra | | 1 |
| 1939 | Silver Threads Among the Gold / Memory Lane | Connie Boswell | | 2 |
| 1939 | (Hol-de-Ay) Start the Day Right / Neighbors in the Sky | Bing Crosby and Connie Boswell with John Scott Trotter and His Orchestra | | 1 |
| 1939 | An Apple for the Teacher / Still the Bluebird Sings | Bing Crosby and Connie Boswell with John Scott Trotter and His Orchestra | | 4 |
| 1939 | A Man and His Dreams / An Apple for the Teacher | Bing Crosby & Connie Boswell with John Scott Trotter and His Orchestra | | 1 |
| 1939 | El Rancho Grande / An Apple for the Teacher | Bing Crosby with The Foursome / Bing Crosby & Connie Boswell | | 1 |
| 1939 | Oh! You Crazy Moon / At Least You Could Say Hello | Connie Boswell | | 1 |
| 1939 | Sunrise Serenade / Wishing | Connie Boswell | | 3 |
| 1939 | Sunrise Serenade / You Grow Sweeter as the Years Go By | Connie Boswell | | 1 |
| 1939 | Sunrise Serenade / Our Love | Connie Boswell / Mary Martin | | 1 |
| 1939 | Thanks for Ev’rything / They Say | Connie Boswell with Woody Herman and His Orchestra | | 1 |
| 1939 | The Lamp Is Low / Stra-Va-Na-Da | Connie Boswell | | 1 |
| 1939 | Thanks for Everything / The Umbrella Man | Connie Boswell | | 1 |
| 1939 | The Umbrella Man / They Say | Connie Boswell with Woody Herman and His Orchestra | | 1 |
| 1939 | Wishing (Will Make It So) / You've Got Me Crying Again | Connie Boswell | | 1 |
| 1940 | Ida, Sweet as Apple Cider / (Ho‐dle‐ay) Start the Day Right | Bing Crosby assisted by The Foursome / Bing Crosby and Connie Boswell | | 1 |
| 1940 | Nobody's Sweetheart / Dinah | Connie Boswell | | 3 |
| 1940 | (Ho‐dle‐ay) Start the Day Right / What’s New? | Bing Crosby & Connie Boswell with John Scott Trotter & His Orchestra | | 1 |
| 1940 | Angel / Someday You'll Find Your Bluebird | Connie Boswell With Victor Young And His Orchestra | | 1 |
| 1940 | Between 18th and 19th on Chestnut Street / Wrap Your Troubles in Dreams | Bing Crosby and Connee Boswell with John Scott Trotter and His Orchestra | | 2 |
| 1940 | Blue Lovebird / Orchids for Remembrance | Connie Boswell | | 1 |
| 1940 | Blueberry Hill / The Nearness of You | Connie Boswell | | 1 |
| 1940 | I Can't Give You Anything but Love, Baby / When It's Sleepy Time Down South | Connie Boswell | | 1 |
| 1940 | Let's Be Buddies / Remember Me | Connie Boswell | | 1 |
| 1940 | My! My! / Never Took a Lesson in My Life | Connie Boswell | | 1 |
| 1940 | On the Isle of May / Gotta Get Home | Connee Boswell with Victor Young and His Orchestra | | 1 |
| 1940 | Oh! You Crazy Moon / Summer Souvenirs | Connie Boswell | | 1 |
| 1940 | Sweet Potato Piper / Between 18th and 19th on Chestnut Street | Bing Crosby assisted by The Foursome / Bing Crosby and Connie Boswell | | 2 |
| 1940 | Stra-Va-Na-Da (The Double Talk Song) / Serenade in the Night | Connie Boswell | | 2 |
| 1940 | The Moon Fell in the River / Somewhere | Connie Boswell | | 1 |
| 1940 | You're the Only Star / You Grow Sweeter as the Years Go By | Connie Boswell | | 1 |
| 1941 | Yes Indeed / Tea for Two | Bing Crosby and Connie Boswell with Bob Crosby’s Bob Cats | | 5 |
| 1941 | A Gay Ranchero / The Clock Song | Connie Boswell | | 1 |
| 1941 | Amapola (Pretty Little Poppy) / You Forgot About Me | Connie Boswell | | 1 |
| 1941 | Deep in a Dream / Charming Little Faker | Connie Boswell | | 1 |
| 1941 | I Hear a Rhapsody / Kerry Dance | Connie Boswell | | 1 |
| 1941 | Nighty-Night / Sand in My Shoes | Connie Boswell | | 1 |
| 1941 | Sweethearts or Strangers / I’ll Keep On Loving You | Connee Boswell | | 2 |
| 1941 | Stormy Weather / Gee! But I Hate to Go Home Alone | Connie Boswell | | 1 |
| 1941 | Tea for Two / Ciribiribin | Bing Crosby & Connie Boswell / Bing Crosby & Andrews Sisters | | 1 |
| 1941 | You Were Meant for Me / I Went Out of My Way | Connie Boswell | | 2 |
| 1941 | Yes Indeed / Chapel in the Valley | Bing Crosby & Connie Boswell with Bob Crosby’s Bob Cats / Bing Crosby with Victor Young & His Orchestra | | 1 |
| 1942 | He Wears a Pair of Silver Wings / Mighty Lak’ a Rose | Connie Boswell | | 1 |
| 1942 | (As long as You're Not in Love with Anyone Else) Why Don't You Fall in Love With Me? / Just a Letter From Home | Connee Boswell | | 1 |
| 1942 | A String of Pearls / My Silent Love | Connie Boswell | | 1 |
| 1942 | Johnny Doughboy Found a Rose in Ireland / Sweet Eloise | Connee Boswell | | 2 |
