The Headies Award for Best Rap Single
The Headies Award for Best Rap Single is an award presented at The Headies, a ceremony that was established in 2006 and originally called the Hip Hop World Awards. It was first presented to Mode 9 in 2006.
Category records
Most wins| Rank | 1st | 2nd |
| Artist | M.I Vector Phyno | Falz Mode 9 Olamide Ice Prince Terry Tha Rapman Naeto C |
| Total wins | 2 Wins | 1 win |
Most nominations
| Rank | 1st | 2nd | 3rd |
| Artist | M.I Olamide Illbliss Phyno | Naeto C | Mode 9 Ice Prince Reminisce |
| Total noms | 5 nominations | 4 nominations | 3 nominations |