| class="wikitable" style="text-align:center; width:45%;" |
| colspan="4"| Best R&B Single |
|---|
| Year
! Nominees
! Result |
|---|
rowspan="6"|2023[{{cite magazine |author1=Paul Grein |title=Rema, Burna Boy Top 2023 Headies Awards: Full Winners List |url=https://www.billboard.com/music/awards/headies-awards-2023-full-winners-list-rema-burna-boy-1235405814/ |magazine=Billboard |accessdate=5 February 2025 |date=September 4, 2023}}]
!"For My Hand" by Burna Boy (featuring Ed Sheeran)
|{{won}} |
| "Mmadu" by CKay
|{{nom}} |
| "Just 4 U" by Dami Oniru
|{{nom}} |
| "Red Wine" by Preye
|{{nom}} |
| "Hard to Find" by Chike (featuring Flavour)
|{{nom}} |
| "Loyal" by Simi featuring Fave
|{{nom}} |
rowspan="6"|2022[{{cite web |title=Full List of 2022 Headies Awards Winners |url=https://www.afrocritik.com/full-list-of-2022-headies-awards-winners/ |website=Afrocritik |accessdate=5 February 2025 |date=September 5, 2022}}]
!"Essence" by Wizkid (featuring Tems)
|{{won}} |
| "Baby Riddim" by Fave
|{{nom}} |
| "Beggie Beggie" by Ayra Starr (featuring CKay)
|{{nom}} |
| "Running (To You)" by Chike (featuring Simi)
|{{nom}} |
| "Promise" by Niniola
|{{nom}} |
| "Sinner" by Adekunle Gold (featuring Lucky Daye)
|{{nom}} |
rowspan="6"|2020[{{cite web |author1=Ralph Okobz |title=See The Complete List Of Winners At The Headies Award Ceremony {{pipe}} #14thHeadies |url=https://notjustok.com/news/complete-full-list-of-winners-at-the-14th-headies-award-ceremony/ |website=NotJustOk |accessdate=5 February 2025 |date=February 22, 2021}}]
!"Tattoo" by Fireboy DML
|{{won}} |
| "Under the Sky" by Praiz
|{{nom}} |
| "Duduke" by Simi
|{{nom}} |
| "Mad" by Sarz and Wurld
|{{nom}} |
| "Bad Influence" by Omah Lay
|{{nom}} |
| "Dangerous Love" by Tiwa Savage
|{{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}}]
!"Gimme Love" by Seyi Shay (featuring Runtown)
|{{won}} |
| "Tipsy" by Odunsi the Engine (featuring Raye)
|{{nom}} |
| "Serenade " by Funbi
|{{nom}} |
| "Uyo Meyo" by Teni
|{{nom}} |
| "Wishes and Butterflies" by Wurld
|{{nom}} |
| rowspan="6"|2018
!"Smile for Me" by Simi
|{{won}} |
| "Tonight" by Nonso Amadi
|{{nom}} |
| "Folashade" by Praiz
|{{nom}} |
| "Let Me Know" by Maleek Berry
|{{nom}} |
| "Romeo & Juliet" by Johnny Drille
|{{nom}} |
| "Love You Baby" by Banky W.
|{{nom}} |
rowspan="6"|2016[{{cite news|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|publisher=pulse}}]
!"Pray for Me" by Darey (featuring Soweto Gospel Choir)
|{{won}} |
| "Love Don't Care" by Simi
|{{nom}} |
| "Made for You" by Banky W.
|{{nom}} |
| "Super Woman" by Wande Coal
|{{nom}} |
| "Aduke" by Tjan
|{{nom}} |
| "Smile" by Shaydee
|{{nom}} |
rowspan="5"|2015[{{cite news|last1=Akan|first1=Joey|title=Headies 2015: Check out the complete nomination list|url=http://www.pulse.ng/buzz/headies-2015-check-out-the-complete-nomination-list-id4215323.html|accessdate=15 May 2018|publisher=pulse}}]
!"Wish Me Well" by Timi Dakolo
|{{won}} |
| "Heartbeat" by Praiz
|{{nom}} |
| "Baby Daddy" by Iyanya
|{{nom}} |
| "Say You Love Me" by Leriq (featuring Wizkid)
|{{nom}} |
| "Do the Right Thing" by Cobhams Asuquo (featuring Bez)
|{{nom}} |
rowspan="4"|2014[{{cite web|title=The Headies Awards 2014 – Full Winners List - INFORMATION NIGERIA|url=http://www.informationng.com/2014/12/the-headies-awards-2014-full-winners-list.html|website=INFORMATION NIGERIA|accessdate=15 May 2018|date=15 December 2014}}]
!"Let Somebody Love You" by 2face Idibia
|{{won}} |
| "Iyawo Mi" by Timi Dakolo
|{{nom}} |
| "Plan B" by Wande Coal
|{{nom}} |
| "Don Gordon" by Burna Boy
|{{nom}} |
rowspan="5"|2013[{{cite news|title=Olamide wins big @ Headies 2013 + full list of winners - Vanguard News|url=https://www.vanguardngr.com/2013/12/olamide-wins-big-headies-2013-full-list-winners/|accessdate=20 May 2018|work=Vanguard News|publisher=vanguard|date=27 December 2013}}]
!"Good Good Loving" by Banky W.
|{{won}} |
| "Don't Let Go" by Capital Femi
|{{nom}} |
| "Like to Party" by Burna Boy
|{{nom}} |
| "Rich & Famous" by Praiz
|{{nom}} |
| "Omote" by Ese Peters
|{{nom}} |
rowspan="5"|2012[{{cite news|title=Psquare, Bez lead Headies 2012 nominees list - Vanguard News|url=https://www.vanguardngr.com/2012/08/headies-2012-nominees-list-released-psquare-bez-leads-park/|accessdate=20 May 2018|work=Vanguard News|publisher=vanguard|date=28 August 2012}}][{{cite news|title=Vector, DavidO, Psquare clear Headies awards|url=https://www.channelstv.com/2012/10/21/vector-davido-psquare-clear-headies-awards/|accessdate=20 May 2018|work=Channels Television|date=21 October 2012}}]
!"Soundtrack" by May D
|{{won}} |
| "Private Trips" by Wande Coal
|{{nom}} |
| "That Stupid Song" by Bez (featuring Praiz)
|{{nom}} |
| "Nawti" by Olu Maintain
|{{nom}} |
| "Love Me (3x)" by Tiwa Savage
|{{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}}]
!"The Way You Are" by Darey
|{{won}} |
| "Only Me" by 2 Face Idibia
|{{nom}} |
| "I Gat Money" by Capital Femi (featuring Eedris Abdulkareem)
|{{nom}} |
| "For A Minute" by Waje
|{{nom}} |
| "Oyi" (Remix) by Flavour (featuring Tiwa Savage)
|{{nom}} |
| rowspan="5"|2010
!"Strong Ting" by Banky W.
|{{won}} |
| "Never Felt a Love" by Capital Femi
|{{nom}} |
| "I Love You" by P-Square
|{{nom}} |
| "No Stars" by Darey
|{{nom}} |
| "Overkillin" by Djinee
|{{nom}} |