| class="wikitable" style="text-align:center; width:40%;" |
| colspan="4"|Best Rap Single |
|---|
| Year
! Nominees
! Result |
|---|
rowspan="5" |2020[{{Cite web|date=2020-12-07|title=Headies 2020: All the nominees|url=https://www.musicinafrica.net/magazine/headies-2020-all-nominees|access-date=2021-02-21|website=Music In Africa|language=en}}][{{Cite web|date=2021-02-21|title=Here is the complete list of winners at the 14th Headies|url=https://www.pulse.ng/entertainment/music/here-is-the-complete-list-of-winners-at-the-14th-headies-featuring-burna-boy-fireboy/7e1j2gz|access-date=2021-02-21|website=Pulse Nigeria|language=en-US}}]
!"Bop Daddy" – Falz (featuring Ms Banks)
|{{won}} |
| "OGB4IG" – Reminisce
|{{nom}} |
| "Shut Up" – Blaqbonez
|{{nom}} |
| "Country" – Illbliss
|{{nom}} |
| "Get the Info" – Phyno (featuring Falz, Phenom)
|{{nom}} |
rowspan="5"|2019[{{cite web |author1=Gbenga Bada |title=Headies 2019: Here are all the winners at the 13th edition of music award |url=https://www.pulse.ng/entertainment/music/headies-2019-here-are-all-the-winners-at-13th-edition-of-music-award/peegxqv |publisher=Pulse Nigeria |accessdate=20 October 2019 |date=October 20, 2019}}]
!"Talk" – Falz
|{{won}} |
| "We Don't Do That Over Here" – Hotyce
|{{nom}} |
| "40 ft Container" – Illbliss (featuring Olamide)
|{{nom}} |
| "Sacrifice" – Payper Corleone (featuring Alpha Ojini)
|{{nom}} |
| "Gang Gang" – A-Q (featuring Loose Kaynon)
|{{nom}} |
rowspan="5"|2018[{{cite web |author1=Billy Praise |title=The HEADIES 2018: Full List Of Winners. |url=https://guardian.ng/life/music/the-headies-2018-full-list-of-winners/ |publisher=Guardian Life |accessdate=16 March 2019 |date=5 May 2018}}]
!"You Rappers Should Fix Up Your Lives" – M.I
|{{won}} |
| "Something Lite" – Falz (featuring Ycee)
|{{nom}} |
| "Link Up" – Phyno (featuring Burna Boy and M.I)
|{{nom}} |
| "Up To You" – Show Dem Camp (featuring Funbi)
|{{nom}} |
| "Me Versus Me" – Ice Prince
|{{nom}} |
rowspan="6"|2016[{{cite web|last1=Akan|first1=Joey|title=Headies 2016, Full Winners List|url=http://www.pulse.ng/buzz/headies-2016-full-winners-list-id5929550.html|accessdate=15 May 2018}}][{{cite web|title=The Headies Awards 2016: Complete list of Nominees - INFORMATION NIGERIA|url=http://www.informationng.com/2016/11/headies-awards-2016-complete-list-nominees.html|website=INFORMATION NIGERIA|accessdate=15 May 2018|date=9 November 2016}}]
!"Eyan Mayweather" – Olamide
|{{won}} |
| "Asamalekun" – Reminisce
|{{nom}} |
| "Jagaban" – Ycee
|{{nom}} |
| "Chukwu Agozi Go Gi" – Illbliss
|{{nom}} |
| "Agu Ji Ndi Men" – A-Q
|{{nom}} |
| "Show You Something" – Boogey
|{{nom}} |
rowspan="5"|2015[{{cite news|url=http://www.leadership.ng/entertainment/489430/olamide-timi-dakolo-ycee-win-big-headies-2015|title=Olamide, Timi Dakolo, YCee Win Big At HEADIES 2015|work=Leadership Newspaper|last=Abulude|first=Samuel|date=6 January 2016|accessdate=23 January 2016}}]
!"King Kong" – Vector
|{{won}} |
| "Bank Alert" – Illbliss
|{{nom}} |
| "Bad Belle" – M.I
|{{nom}} |
| "Local Rappers" – Reminisce (featuring Olamide & Phyno)
|{{nom}} |
| "T.R" – G.O.D
|{{nom}} |
rowspan="6"|2014[{{cite web|title=Nigeria: Headies 2014 - Davido, Olamide, Patoranking, Mavins Win Big, Wizkid Missing|url=http://allafrica.com/stories/201412152201.html|publisher=allAfrica|accessdate=16 December 2014|date=15 December 2014}}]
!"Parcel" – Phyno
|{{won}} |
| "Dope Money" – Olamide (featuring Phyno)
|{{nom}} |
| "Shots on Shots" – Ice Prince and Sarkodie
|{{nom}} |
| "Rap It Up" – Posly TD
|{{nom}} |
| "Deaf" – Eva Alordiah
|{{nom}} |
| "WTF"- Illbliss
|{{nom}} |
rowspan="5"|2013[{{cite web|url=http://www.thisdaylive.com/articles/olamide-heads-the-headies/167539/ |title=Olamide Heads The Headies, Articles |publisher=Thisday Live |date=2013-12-29 |accessdate=2014-05-17}}][{{cite web|author=|url=http://www.vanguardngr.com/2013/12/olamide-wins-big-headies-2013-full-list-winners/ |title=Olamide wins big @ Headies 2013 + full list of winners |publisher=Vanguardngr.com |date=2013-12-27 |accessdate=2014-05-17}}]
!"Man of the Year" – Phyno
|{{won}} |
| "Anam Achi Kwanu" – Illbliss (featuring Phyno)
|{{nom}} |
| "Durosoke" – Olamide
|{{nom}} |
| "2 Musshh" – Reminisce
|{{nom}} |
| "Ghost Mode" – Phyno (featuring Olamide)
|{{nom}} |
rowspan="5"|2012[{{cite web|url=http://www.channelstv.com/2012/10/21/vector-davido-psquare-clear-headies-awards/ |title=Vector, DavidO, Psquare clear Headies awards |publisher=Channelstv.com |date= |accessdate=2014-05-17}}][{{cite web|author=|url=http://www.vanguardngr.com/2012/08/headies-2012-nominees-list-released-psquare-bez-leads-park/ |title=Psquare, Bez lead Headies 2012 nominees list |publisher=Vanguardngr.com |date=2012-08-28 |accessdate=2014-05-17}}]
!"Angeli" – Vector (featuring 9ice)
|{{won}} |
| "Too Much Money" – Iceberg Slim
|{{nom}} |
| "Shutdown" – Phyno
|{{nom}} |
| "Oh My Gosh" – Yung6ix
|{{nom}} |
| "Young Erikina" – Olamide
|{{nom}} |
rowspan="5"|2011[{{cite web|author=Alhaji Sorie Kamara Says |url=http://www.goldenicons.com/hip-hop-world-awards/ |title=Hip-Hop World Awards |publisher=Golden Icons |date= |accessdate=2014-05-17}}][{{cite web|url=http://fabmagazineonline.com/the-headies-2011-nominees-announced/ |title=The Headies 2011 Nominees Announced |publisher=Fabmagazineonline.com |date=2011-08-02 |accessdate=2014-05-17}}]
!"Oleku" – Ice Prince (featuring Brymo)
|{{won}} |
| "Ten Over Ten" – Naeto C
|{{nom}} |
| "Boys Are Not Smiling" – Terry Tha Rapman
|{{nom}} |
| "Eni Duro" – Olamide
|{{nom}} |
| "She and My Swagga" – Ruggedman (featuring Ice Prince)
|{{nom}} |
| rowspan="5"|2010
!"Sample" (Remix) – Terry Tha Rapman (featuring Stereo Man and Pherowshuz)
|{{won}} |
| "Finest" – Knight House (featuring Sauce Kid and Teeto)
|{{nom}} |
| "Somebody Wants to Die" – M.I
|{{nom}} |
| "Owo Ati Swagger" – Cartiair
|{{nom}} |
| "Ako Mi Ti Poju" – Naeto C
|{{nom}} |
rowspan="4"|2009[{{cite web|author=Source: http://.nigeriafilms.com |url=http://www.modernghana.com/movie/4826/3/hip-hop-world-awards-2009-winners.html |title=Hip Hop World Awards 2009 winners |publisher=Modernghana.com |date=2009-05-17 |accessdate=2014-05-17}}][{{cite web|url=http://www.bellanaija.com/2009/03/10/hiphop-world-awards-2009-nominees-announced/ |title=HipHop World Awards 2009 Nominees Announced |publisher=Bella Naija |date=2009-03-12 |accessdate=2014-05-17}}]
!"Kini Big Deal" – Naeto C
|{{won}} |
| "Wa Wa Alright" – Kel
|{{nom}} |
| "Talking to You" – Mode 9 (featuring Banky W.)
|{{nom}} |
| "Safe" – M.I (featuring Djinee)
|{{nom}} |
rowspan="4"|2008[{{cite web|author=Greg |url=http://worldhiphopmarket.com/the-hip-hop-world-awards/ |title=The Hip Hop World Awards |publisher=World Hip Hop Market |date=2008-03-31 |accessdate=2014-05-17}}]
!"Crowd Mentality" - M.I
|{{won}} |
| "Mo" – Rooftop MC
|{{nom}} |
| "Stylee" – DJ Jimmy Jatt, Mode 9, 2Face Idibia & Elajoe
|{{nom}} |
| "U know My P" – Naeto C
|{{nom}} |
| 2006
!"Elbow Room" – Mode 9
|{{won}} |