| class="wikitable"
|+
! colspan="3" | Best Pop Single |
| Year
|Nominees
|Result |
rowspan="6" |2019[{{Cite web |date=2019-10-01 |title=Headies 2019 Nominees List: Davido, Wizkid And Burna Boy Vie For Top Awards |url=https://guardian.ng/life/headies-2019-nominees-list-davido-wizkid-and-burna-boy-vie-for-top-awards/ |access-date=2023-02-04 |website=The Guardian Nigeria News - Nigeria and World News |language=en-US}}]
|Ye – Burna Boy
|{{nom}} |
| Wetin We Gain – Victor AD
|{{nom}} |
| Fake Love – Starboy (featuring Duncan Mighty and Wizkid)
|{{nom}} |
| Case – Teni
|{{won}} |
| Jealous – Fireboy DML
|{{nom}} |
| Baby – Joeboy
|{{nom}} |
rowspan="6" |2018[{{Cite web |date=2018-04-13 |title=Headies 2018: Full list of nominees |url=https://punchng.com/headies-2018-full-list-of-nominees/ |access-date=2023-02-04 |website=Punch Newspapers |language=en-US}}]
|Mad Over You – Runtown
|{{nom}} |
| All Over – Tiwa Savage
|{{nom}} |
| Yeba – Kiss Daniel
|{{nom}} |
| Iskaba – Wande Coal & DJ Tunez
|{{nom}} |
| If – Davido
|{{won}} |
| Fia – Davido
|{{nom}} |
| rowspan="8" |2016
|Mama – Kiss Daniel
|{{nom}} |
| Final (Baba Nla) – Wizkid
|{{nom}} |
| Pick Up – Adekunle Gold
|{{nom}} |
| Osinachi – Humblesmith (featuring Davido)
|{{nom}} |
| Reggae Blues – Harrysong (featuring Orezi, Iyanya, Olamide, Kcee)
|{{won}} |
| Emergency – D’banj
|{{nom}} |
| Fada Fada – Phyno (featuring Olamide)
|{{nom}} |
| Money – Timaya (featuring Flavour)
|{{nom}} |
rowspan="6" |2015[{{Cite news |title=Headies Awards 2015: Full List Of Winners |language=en-US |work=Channels Television |url=https://www.channelstv.com/2016/01/02/headies-awards-2015-full-list-of-winners/ |access-date=2023-02-04}}]
|Godwin – Korede Bello
|{{won}} |
| Ojuelegba – Wizkid
|{{nom}} |
| Collabo – P-Square (featuring Don Jazzy)
|{{nom}} |
| My Woman, My Everything – Patoranking (featuring Wande Coal)
|{{nom}} |
| Woju – Kiss Daniel
|{{nom}} |
| Bobo – Olamide
|{{nom}} |
rowspan="7" |2014[{{Cite web |last=Alonge |first=Tinya |date=2014-09-30 |title=THE HEADIES 2014 NOMINEES LIST |url=https://culturecustodian.com/the-headies-2014-nominees-list/ |access-date=2023-02-04 |website=The Culture Custodian (Est. 2014.) |language=en-GB}}]
|Dorobucci – Mavin Crew
|{{won}} |
| Aye – Davido
|{{nom}} |
| Johnny – Yemi Alade
|{{nom}} |
| Pull Over – Kcee (featuring Wizkid)
|{{nom}} |
| Double Wahala – Oritse Femi
|{{nom}} |
| Caro – Starboy (featuring Wizkid and L.A.X)
|{{nom}} |
| Surulere – Dr. Sid (featuring Don Jazzy)
|{{nom}} |
rowspan="6" |2013[{{Cite web |last=Alonge |first=Tinya |date=2014-09-30 |title=THE HEADIES 2014 NOMINEES LIST |url=https://culturecustodian.com/the-headies-2014-nominees-list/ |access-date=2023-02-04 |website=The Culture Custodian (Est. 2014.) |language=en-GB}}]
|Ihe Neme – 2Face Idibia
|{{won}} |
| The Kick - Wande Coal (featuring Don Jazzy)
|{{nom}} |
| Gobe - Davido
|{{nom}} |
| Catching Cold - Tunde Ednut
|{{nom}} |
| Ur Waist – Iyanya
|{{nom}} |
| Goody Bag – D’Prince
|{{nom}} |
rowspan="5" |2012[{{Cite web |last=theodore |first=nyingifa |date=2013-10-16 |title=Headies 2012 Nominees List Out!...PSquare, Bez, Ice Prince & Wizkid top list |url=https://www.pulse.ng/gist/headies-2012-nominees-list-outpsquare-bez-ice-prince-and-wizkid-top-list/tz74hfp |access-date=2023-02-04 |website=Pulse Nigeria |language=en}}]
|Dami Duro – Davido
|{{nom}} |
| Oliver Twist – D’Banj
|{{nom}} |
| Gaga Crazy – Chuddy K
|{{nom}} |
| Chop My Money – P-Square (featuring Akon and May D)
|{{nom}} |
| Kukere – Iyanya
|{{won}} |
rowspan="5" |2011[{{Cite web |last=Nigeria |first=Information |date=2011-08-03 |title=Headies (Hip hop World Awards) 2011 Nominees List…..Wizkid, Don Jazzy Get Nominations |url=https://www.informationng.com/2011/08/headies-hip-hop-world-awards-2011-nominees-list-wizkid-don-jazzy-get-nominations.html |access-date=2023-02-04 |website=Information Nigeria |language=en-US}}]
|Give It To Me – D’Prince (featuring D'banj)
|{{nom}} |
| Pop Champaign – Dr. Sid (featuring D'banj)
|{{won}} |
| Holla at Your Boy – Wizkid
|{{nom}} |
| Mr Endowed – D’banj
|{{nom}} |
| Fimile – Kas
|{{nom}} |