The award for Best Wargaming Article is sponsored by Gripping Beast, and was Initiated in 1996; it is awarded by the Editor to the best wargaming article in the year.
| Year | Winner | Article | Slingshot |
| 2025 | Bruno Servili | Maldon 991 AD as a card-assisted wargame project | 356, 359 |
| 2024 | Steve Neate | The Maccabean Revolt: Seven Games in an Evening Using Command & Colours | 355 |
| 2023 | Nick Harbud | If You Go Down To The Woods Today | 350 |
| 2020 | Paul Innes | Tactica II: A Ruleset Analysis | 334 |
| 2019 | Nick Harbud | Chances Are | 328 |
| 2018 | Chris Hahn | Wargaming War Wagons | 320 |
| 2017 | Chris Hahn | Paraetacene | 317 |
| 2016 | Chris Hahn | Refight accounts and rules commentaries across a wide range of battles | 310 |
| 2015 | Roy Boss | Retrospective of the Society’s History | 301 |
| 2014 | Steven Neate | Converting Command & Colors: Ancients to the tabletop | 299 |
| 2013 | Richard Taylor | War, Games and Wargames | 292 |
| 2012 | Mark Fry | Teutonic Indigestion | 285 |
| 2011 | Julian Lorriman | Quick Resolution for Ancient Battles | 280 |
| 2010 | Aaron Bell | Generating Lost Battles | 272 |
| 2009 | Adrian Goldsworthy | Thinking about Romans – EIR for WAB | |
| 2008 | Paul Burton | Campaigns for Wargamers series | |
| 2007 | Dr Sahid Mohamed Dadabhoy | Article on the frustrations of a Muslim wargamer | |
| 2006 | Mike Tittensor | Do Ancients Stop at Qadesh | |
| 2005 | Graham Evans | De Matrica Bellae | |
| 2004 | Scott Robinson | Successor Battles | |
| 2003 | Steven Neate | Wargaming Hasmonean Judea | |
| 2002 | David Davidson | May the Sky not Fall on your Head | |
| 2001 | Phil Halewood | A Ridge too Far – Two Refights of Granicus | |
| 2000 | Nick Harbud | De Bellis Hibernicus – Rules for Mediaeval Irish Warfare | |
| 1999 | Peter Hall | Wargaming Alexander in the East | |
| 1998 | Phil Halewood & Carl Luxford | The Battle of Al Qadisayyah – 637 AD | |
| 1997 | John Graham-Leigh | Solo Campaigning | |
| 1996 | Carl Luxford | Wargaming with Arrian against the Alans |