Only happened twice in the history of my chart by the looks of it!

 

2019 - Cavetown (Green, Home, Telescope)

2020 - Declan McKenna (Beautiful Faces, The Key To Life On Earth, Be An Astronaut)

2021 - None

2022 - None

2023 - Sigur Rós (4)

 

A couple came close like Sleeping At Last, VICTORIA and Gísli Gunnarsson (also Highasakite, Ólafur Arnalds and LANKS but in 2 calendar years separated within a year of duration).

8

2023 | The Kid LAROI: I Can't Go Back to the Way It Was (Intro) | LOVE AGAIN | I GUESS IT'S LOVE? | Forever & Again | TOO MUCH | WHAT JUST HAPPENED | BLEED | WHAT'S THE MOVE?

 

6

2019 | Why Don't We: Big Plans | Cold in LA | Unbelievable | Come to Brazil | I Still Do | What Am I

 

5

2020 | The Kid LAROI: NEED YOU MOST (So Sick) | SO DONE | ALWAYS DO | Reminds Me of You | WITHOUT YOU

 

4

2012 | One Direction: More Than This | Live While We're Young | Little Things | Kiss You

2014 | Hunter Hayes: More Than I Should | I Want Crazy | Invisible | Tattoo

2017 | The Vamps: Middle of the Night | Hands | Staying Up | Personal

2018 | Why Don't We: Trust Fund Baby | Hooked | Talk | 8 Letters

2018 | Rita Ora: For You | Girls | Let You Love Me | Only Want You

2018 | Matteo Markus Bok: El Ritmo (AHI AHI AHI) | In the Middle | Shallow | Mrs Lonely

2021 | Justin Bieber: Anyone | Hold On | Unstable | STAY

2021 | Boy In Space: Dance Alone | Remember Me | Sucker Punch | Paradise

2022 | Benson Boone: ROOM FOR 2 | In the Stars | Better Alone | Before You

2023 | Sarcastic Sounds: Stumbling | Jaycee | Hero | Better Half

2023 | Benson Boone: Sugar Sweet | What Was | Little Runaway | To Love Someone

2024 | The Kid LAROI: HEAVEN | Still Yours | NIGHTS LIKE THIS | GIRLS

 

3

2012 | Justin Bieber: Boyfriend | Turn to You (Mothers' Day Dedication) | As Long As You Love Me

2012 | Delta Goodrem: Sitting On Top of the World | Dancing With a Broken Heart | Wish You Were Here

2013 | Cody Simpson: Wish U Were Here | Pretty Brown Eyes | La Da Dee

2013 | One Direction: One Way or Another (Teenage Kicks) | Best Song Ever | Story of My Life

2014 | Ariana Grande: Problem | Break Free | Bang Bang

2014 | Iggy Azalea: Fancy | Problem | Black Widow

2014 | The Vamps: Last Night | Somebody to You | Oh Cecilia (Breaking My Heart)

2019 | Alec Benjamin: Must Have Been the Wind | Jesus in LA | Mind is a Prison

2019 | Harry Styles: Lights Up | Watermelon Sugar | Adore You

2020 | Boy In Space: Caroline | Still the Same | Therapy

2020 | Ulrik Munther: Gloom. | C'est la vie | Don't Worry

2021 | Alec Benjamin: The Older You Get | Change My Clothes | Older

2021 | The Kid LAROI: Unstable | STAY | STILL CHOSE YOU

2022 | glaive: poison | minnesota is a place that exists | three wheels and it still drives!

2022 | Sarcastic Sounds: Disappointment | ohf***imnotok | might be this

 

The Kid LAROI has achieved 3+ #1s in a calendar year on four occasions out of a possible five to date! Benson Boone managed it in 2022 and 2023 (he debuted in 2021 but it wasn't possible with only one song released), and has two #1s in 2024 so far, so he could make it a hat-trick this year. Nobody else has had more than a single #1 so far this year yet.