| Pre-Season Races: |
| Date | Race | Sponsor | Location |
| 4/20/08 | Kala Kukea Iron Race | Hui Nalu | Maunalua Bay |
| 3/22/08 | Puuloa OCC Iron Race | Puuloa OCC | Keehi Lagoon |
| 4/19/08 | Kahiau Ironman Race | Keahiakahoe | Keehi Lagoon |
| 5/10/08 | Kala’ Iomalulani Race | Keahiakahoe | Kailua/Kaneohe/Kahaluu |
| 5/17/08 | George Perry Keiki | Lanikai | Kailua Beach Park |
| Regatta Season Races: |
| Date | Race | Sponsor | Location |
| 6/01/08 | Clement D. Pa’aina Regatta | Healani CC | Keehi Lagoon |
| 6/08/08 | King Kamehameha Regatta | Kailua CC | Kailua Beach Park |
| 6/15/08 | Leeward Kai Father's Day | Leeward Kai CC | Nanakuli Beach Park |
| 6/22/08 | Waimanalo Canoe Club | Waimanalo CC | Waimanalo Beach |
| 7/04/08 | Walter J. MacFarlane Regatta
| Outrigger CC | Waikiki Beach |
| 7/13/08 | John D. Kaupiko Regatta
| Hui Nalu CC | Keehi Lagoon |
| 7/20/08 | O.H.C.R.A. Championships | OHCRA | Keehi Lagoon |
| 8/02/08 | STATE CHAMPIONSHIPS | HCRA | KEEHI LAGOON |
| Long Distance Races: |
| Date | Race | Sponsor | Location |
| 8/10/08 | Kaena Challenge | Makaha CC | Sunset Beach Park to Makaha Beach |
| 8/17/08 | Duke Kahanamoku Race | Lanikai CC | Kailua Beach Park to Hilton Pier |
| 8/23/08 | Kailua Bay Iron Men | Kailua CC | Kailua Beach Park |
| 8/24/08 | Dad's Center Race | Outrigger CC | Kailua Beach Park to Outrigger CC |
| 9/07/08 | E Lau Hoe | OHCRA | Maunalua Bay to Nanakuli Beach Park |
| 9/14/08 | Henry Ayau Memorial Race | Hui Lanakila CC | Maunalua Bay to Nanakuli Beach Park |
| 10/12/08 | MOLOKA'I HOE | OHCRA | MOLOKA'I to OAHU |
