| MULTIPLE NNA WINNERS – 4 OR MORE (INDIVIDUAL AND CO-WINNERS ONLY, NO TEAM AWARDS) | ||
| NAME | No. | CATEGORIES |
| Serge Chapleau, La Presse | 8 | Editorial Cartooning ’97, ’99, ’00, ’02, ’03, ’07, ’12, ’19 |
| Jacquie McNish, Globe and Mail | 8 | Business ’92, ’02, ’07, ’09, ’10, ’12, ’15; Arts and Entertainment ’15 |
| Stephanie Nolen, Globe and Mail | 8 | International ’03, ’04, ’11; Explanatory Work ’07, ’09; Arts and Entertainment ’11, ’12; Business ’19 |
| Brian Gable, Globe and Mail, Regina Leader-Post | 7 | Editorial Cartooning ’86, ’95, ’01, ’05, ’09, ’10, ’16 |
| Michèle Ouimet, La Presse, Montréal | 7 | Investigations ’07, ’10; Long Feature ’09; International ’12, ’13; Columns ’13; Short Feature ’15 |
| Roy Peterson, Vancouver Sun | 7 | Editorial Cartooning ’68, ’75, ’84, ’90, ’94, ’96, ’98 |
| Grant Robertson, Calgary Herald, Globe and Mail | 7 | Business ’04, ’14; Explanatory Work ’11, ’16; Sports ’11; Short Feature ’13; Long Feature ’18 |
| Bruce MacKinnon, Halifax Chronicle-Herald | 6 | Editorial Cartooning ’92, ’93, ’13, ’14, ’15, ’17 |
| Mark MacKinnon, Globe and Mail | 6 | Business ’99, ’11; Short Features ’03; Breaking News ’12; International ’14, ’16 |
| Duncan Macpherson, Toronto Star | 6 | Editorial Cartooning ’59, ’60, ’62, ’65, ’70, ’72 |
| Bruno Schlumberger, Ottawa Citizen | 6 | Feature Photo ’82, ’87, ’07, ’09; News Photo ’97; News Feature Photo ’09 |
| Doug Saunders, Globe and Mail | 5 | Critical Writing ’98, ’99, ’00; Columns ’05, ’12 |
| John Stackhouse, Globe and Mail | 5 | Feature Writing ’94, ’99; Business ’97; International ’97, ’99 |
| David Baines, Vancouver Sun | 4 | Business ’89, ’98, ’00, ’05 |
| Ian Brown, Globe and Mail | 4 | Feature Writing ’84; Explanatory Work ’03; Long Feature ’05, ’07 |
| Edgar A. Collard, Montreal Gazette | 4 | Editorials ’49, ’50, ’59, ’68 |
| Marcus Gee, Globe and Mail | 4 | Columns ’98; Editorials ’01; Short Feature ’17, ’19 |
| Marty Klinkenberg, New Brunswick Telegraph-Journal, Globe and Mail | 4 | Arts and Entertainment ’07, ’10; Sports ’09, ’16 |
| Larry MacDougal, Ottawa Citizen, Calgary Herald, Canadian Press | 4 | News Photo ’81, ’05; Sports Photo ’89, ’95 |
| Lucas Oleniuk, Toronto Star | 4 | News Photo ’04; News Feature Photo ’08, ’10; Sports Photo ’16 |
| Peter Power, Toronto Star | 4 | Feature Photo ’96, ’01, ’12; Sports Photo ’02 |
| Boris Spremo, Globe and Mail, Toronto Star | 4 | Feature Photo ’62, ’63, ’68, ’77 |
| Paul Watson, Toronto Star | 4 | Spot News Photo ’93; International ’93, ’96; Investigations ’94 |
| Patrick White, Globe and Mail | 4 | Long Feature ’11, ’14; Beat Reporting ’16; Short Feature ’18 |
| Peter Worthington, Toronto Telegram, Toronto Sun | 4 | Feature Writing ’62; Staff Corresponding ’69; Editorials ’72; Enterprise Reporting ’78 |
| Geoffrey York, Globe and Mail | 4 | International ’09, ’10, ’19; Business ’19 |