Objectives: The aim of the present study was to compare and investigate the relationship between 500 m on-water performance and physical characteristics in elite and sub-elite outrigger canoe paddlers. Methods: A total of 16 males participated in the study including eight elite paddlers (age: 24.8 ± 10.5 yrs., total paddling experience: 12.5 ± 5.2 yrs.) and eight sub-elite paddlers (age: 34.4 ± 15.4 yrs., total paddling experience: 6.8 ± 5.2 yrs.). Body mass, height, sitting height, arm span, arm length, body fat percentage, 50 kg muscular endurance (bench press and bench pull), peak oxygen uptake (VO2peak) and Wingate performance (30 sec maximal effort) were assessed and subsequently correlated with 500 m outrigger canoeing performance at a national championship’s regatta. Results: When group data were combined, moderate to strong correlations were found between 500 m outrigger canoeing performance and absolute VO2peak (r = -0.61), upper limb length (r = -0.60) 50 kg bench press (r = -0.56), total paddling experience (r = -0.53), body mass (r = -0.51), sitting height (r = -0.51), singles paddling experience (r = -0.49), height (r = -0.48) and Wingate distance (r = -0.42). When groups were compared, elite paddlers showed significantly greater Wingate mean power and distance, paddling experience and 500 m on-water performance times than sub-elite paddlers (p < 0.05). However, there were no significant differences in anthropometrical measures, muscular endurance and VO2peak between the two groups (p < 0.05). Conclusion: VO2peak and upper limb length were the best predictors of performance over the 500 m sprint distance across the entire group. Thirty-second Wingate mean power and distance, years of paddling experience and subsequent 500 m on-water performance differentiated elite from sub-elite paddlers.