The outcomes of fights often affect the fitness of males by determining their access to mates. ‘Winner-loser’ effects, where winners often win their next contest, but losers tend to lose, can therefore influence how males allocate resources towards traits under pre- and post-copulatory sexual selection. We experimentally manipulated the winning/losing experiences of size-matched male Gambusia holbrooki for either a day, a week or three weeks to test whether prior winning/losing experiences differentially affect the plasticity of male investment into either mating effort (pre-copulatory) or ejaculates (post-copulatory). Winners had better pre-copulatory outcomes than losers for three of the four traits we measured: number of mating attempts, number of successful attempts, and time spent with the female. Winners also produced faster sperm than losers, but there was no difference in total sperm counts. Interestingly, absolute male size, an important predictor of fighting success, mediated the effect of winning or losing on how long males then spent near a female. Smaller winners spent more time with the female than did larger winners, suggesting that how males respond to prior social experiences is size-dependent. We discuss the general importance of controlling for inherent male condition when comparing male investment into condition-dependent traits.