The following individuals and posts were the recipients of an award and/or scholarship for the 2018-2019 year:
| Program | Name | Award |
| Boys State | Geoffrey Astor, Post #130 (Ft. Dodge) | SAL Band Award |
| Blake Perkins, Post #219 (Arlington) | SAL Chorus Award | |
| Samuel Sirna, Post #59 (Story City) | Andy Haverman Scholarship | |
| Trejahn Manning, Post #374 (Hiland Park, Des Moines) | Donald E. Johnson Outstanding Citizen Award | |
| Patrick Junker, Post #403 (Van Meter) | Boys State Governor Scholarship & Boys Nation | |
| Samuel Harrison, Post #199 (Sioux Center) | SAL Scholarship Lt. Governor | |
| Luke Prendergast, Post #653 (Denver) | Boys Nation | |
| Kyler Sander, Post #31 (Lake City) | Boys Nation Alternative 1 | |
| Animesh Joshi, Post #620 (West Des Moines) | Boys Nation Alternative 2 | |
| Jacob James, Post #2 (Council Bluffs) | Samsung Finalist | |
| Cole Lindaman, Post #246 (Clarion) | Legal Merit Award | |
| John Alex Baker, Post #98 (Clarinda) | Keith Baker Scholarship | |
| Isaiah Wagner, Post #274 (Baldwin Patterson, Des Moines) | SAL Highway Patrol Award | |
| Boy Scouts | Ethan Hoefler, Post #137 (Dyersville) | Eagle Scout of the Year |
| Hunter Wright, Post #238 (DeWitt) | Runner Up | |
| Logan Van Itallie, (Post not listed) | 3rd Place | |
| Fifth Grade Flag Essay | Sherry Tang, Post #347 (Le Claire) | First Place |
| Kloey Rine, Post #88 (Shenandoah) | Second Place | |
| Jaime Self, Post #407 (Unionville) | Third Place | |
| Educator of the Year | Kevin Mundt, Post #430 (Durant) | First Place |
| Firefighter of the Year | Zackery Harvey, Post #182 (Eldora) | Recipient & National Finalist |
| LEO of the Year | Jason Grubbs, Post #37 (Ames) | Recipient |
| Oratorical | Patrick Junker, Post #403 (Van Meter) | First Place |
| Thomas Evans, Post #607 (Breda) | Second | |
| Jessica Cline, Post #298 (Marion) | Third | |
| CPR Community Service | Lyle W. Barnes Post #398 (Quimby) | Hanford Post Trophy |
| USS San Diego Post #207 (La Porte City) | Becker-Chapman Trophy | |
| Stinocher Post #460 (Solon) | Davenport Trophy | |
| Wasmer Post #241 (Le Mars) | Warren Post Trophy | |
| Marion Post #298 (Marion) | Frank Lewis Glick Trophy | |
| Baldwin Patterson Post #274 (Des Moines) | Ames Post Trophy | |
| Second District (85%) | William C. Rathke Award | |
| Homer Hall Post #66 (Charter Oak) | God and Country Award | |
| Lake Park Post #371 (Lake Park) | Educate American Award | |
| Marion Post #298 (Marion) | Public Relations Award | |
| Doornink-Brunsting Post #199 (Sioux Center) | Operation Troop Support Award | |
| Scherrman-Peterson Post #656 (Farley) | Step Up Award | |
| Wasmer Post #241 (Le Mars) | Service to Community, State & Nation Award | |
| CPR Children & Youth | Scherrman Peterson Post #656 (Farley) | Most Outstanding |
| Howard Cessna Post #136 (Albia) | Overall Runner Up | |
| West Union Post #15 (West Union) | Category 1 Overall | |
| Swisher Post #671 (Swisher) | Category 2 Overall | |
| Wasmer Post #241 (Le Mars) | Category 3 Overall | |
| Marion Post #298 (Marion) | Category 4 Overall | |
| Junior Shooting Sports | Sydney Krejci, Post #374 (Hiland Park, Des Moines) | First Place Overall |
| Adrianna Campos, Post #374 (Hiland Park, Des Moines) | Second Place Overall | |
| Ayden Wells, Post #374 (Hiland Park, Des Moines) | Third Place Overall | |
| Sydney Krejci, Post #374 (Hiland Park, Des Moines) | Age Category 1 – First | |
| Adrianna Campos, Post #374 (Hiland Park, Des Moines) | Age Category 1 – Second | |
| James Masteller, Post #374 (Hiland Park, Des Moines) | Age Category 1 – Third | |
| Ayden Wells, Post #374 (Hiland Park, Des Moines) | Age Category 2 – First | |
| Arion Cartagena, Post #374 (Hiland Park, Des Moines) | Age Category 2 – Second | |
| Cecilia Zaragoza, Post #374 (Hiland Park, Des Moines) | Age Category 2 – Third | |
| Annabell Forbes, Post #457 (Lone Tree) | Age Category 3 – First | |
| Abigail O’Rear, Post #671 (Swisher) | Age Category 3 – Second | |
| Kiara Hallett, Post #27 (Muscatine) | Age Category 3 – Third | |
| Des Moines North, Post #374 (Hiland Park, Des Moines) | First Place Team | |
| Mumm’s Jr. Rifles, Post #457 (Lone Tree) | Second Place Team | |
| Swisher Sharpshooters, Post #671, (Swisher) | Third Place Team | |
| Legionnaire of the Year | Cliff Ripke, Post #288 (Hartley) | Recipient |
| Baseball* | Cody Deardorff, Dubuque Co. Baseball, Post #6 (Dubuque) | 2019 American Legion Baseball Player of the Year Scholarship & plaque (Awarded the following year) |
| Dubuque County Baseball, Post #528 (Cascade), Post #6 (Dubuque), Post #137 (Dyersville), Post #650 (Epworth), Post #656 (Farley) | Championship Team | |
| Woodbury County Baseball, Post #662 (Sgt. Bluff) | Runner Up | |
| IALPA | Bellevue Post #273 | Category 1 – Single Sheet |
| Gladbrook Post #127 | Category 2 – Multiple Sheet | |
| Bellevue Post #273 | Category 3 – Electronic | |
| Dubuque Post #6 | Category 4 – Website | |
| Color Guard Competition | J.L. Shryer American Legion Post #430 (Durant) | Military Open Class & Advance and Retire Colors Class Winners |
*2018 Baseball Player of the Year awarded at 2019 Department Convention – Gannon O’Brien, Dubuque County Baseball, Post #528 (Cascade)