Listing the 56 multiple-time winners of the prestigious Walsh Ironman. There have been two four-time champions, 14 three-time champions and 40 two-time champions going into 2021.
| Titles | First | Last | School(s) | State |
| 4 | David | Taylor | Graham | OH |
| 4 | Zahid | Valencia | St. John Bosco | CA |
| 3 | Braxton | Amos | Parkersburg South | WV |
| 3 | Kurt | Backes | Blair Academy | NJ |
| 3 | Brooks | Black | Blair Academy | NJ |
| 3 | Patrick | Bond | Great Bridge | VA |
| 3 | Cory | Cooperman | Blair Academy | NJ |
| 3 | George | DiCamillo | St. Ignatius | OH |
| 3 | Aaron | Hart | Graham | OH |
| 3 | Mark | Jayne | Lakewood St. Edward | OH |
| 3 | Bo | Jordan | Graham | OH |
| 3 | Jeff | Knupp | Walsh Jesuit | OH |
| 3 | Spencer | Lee | Franklin Regional | PA |
| 3 | Harry | Lester | CVCA | OH |
| 3 | Nathan | Tomasello | CVCA | OH |
| 3 | Chris | Villalonga | Blair Academy | NJ |
| 2 | Andrew | Alton | Central Mountain | PA |
| 2 | Dylan | Alton | Central Mountain | PA |
| 2 | Michael | Beard | Malvern Prep | PA |
| 2 | Mason | Beckman | Reynolds | PA |
| 2 | Mikey | Benefiel | Montini Catholic | IL |
| 2 | David | Carr | Massillon Perry | OH |
| 2 | Ryan | Davis | Blair Academy | NJ |
| 2 | Joe | Dennis | Graham | OH |
| 2 | Cameron | Doggett | Graham | OH |
| 2 | Zack | Esposito | Blair Academy | NJ |
| 2 | A.J. | Ferrari | Allen/Blair Academy | TX/NJ |
| 2 | Adam | Frey | Blair Academy | NJ |
| 2 | Cody | Gardner | Christiansburg | VA |
| 2 | Garrett | Goebel | Montini Catholic | IL |
| 2 | Joe | Heskett | Walsh Jesuit | OH |
| 2 | Ryan | Kinley | Lakewood St. Edward | OH |
| 2 | Matt | Koz | Lakewood St. Edward | OH |
| 2 | Ryan | Lang | Lakewood St. Edward | OH |
| 2 | Nick | Mann | Lakewood St. Edward | OH |
| 2 | Alex | Marinelli | Graham | OH |
| 2 | Trevor | Mastrogiovanni | Blair Academy | NJ |
| 2 | Frank | Mattiace | Blair Academy | NJ |
| 2 | Brent | McBurney | Massillon Perry | OH |
| 2 | Alex | Meade | Caesar Rodney | DE |
| 2 | Eric | Medina | Blair Academy | NJ |
| 2 | Dylan | Milonas | Blair Academy | NJ |
| 2 | Steve | Mocco | Blair Academy | NJ |
| 2 | Mark | Perry | Blair Academy | NJ |
| 2 | Chris | Phillips | Monroeville | OH |
| 2 | Robbie | Preston | Blair Academy | NJ |
| 2 | C.P. | Schlatter | Graham | OH |
| 2 | Dustin | Schlatter | Graham/Massillon Perry | OH |
| 2 | Cohlton | Schultz | Ponderosa | CO |
| 2 | Chase | Singletary | Blair Academy | NJ |
| 2 | Nate | Skonieczny | Walsh Jesuit | OH |
| 2 | Bryan | Snyder | Easton | PA |
| 2 | Kyle | Snyder | Good Counsel | MD |
| 2 | Hunter | Stieber | Monroeville | OH |
| 2 | Logan | Stieber | Monroeville | OH |
| 2 | Anthony | Valencia | St. John Bosco | CA |
