Individually, both near-misses and losses disguised as wins (LDWs) have been seen to exert pro-motivational effects on gambling. However, it is not clear whether both structural characteristics are effective within the same game. Participants (n = 40) played a slot machine simulation. The simulation delivered near-misses, wins and ‘full-misses’. Half the participants also received LDWs that occurred independently of the outcomes on the payline. Valence and motivation ratings were collected after each round. Results showed that the LDW group reported increased valence ratings compared to the no-LDW group. Within the LDW group, trials with LDWs also resulted in increased enjoyment compared to trials without LDWs. We distinguished near-misses falling either side of the payline. Near-misses before the payline (NMB) were rated as more motivational than near-misses after the payline (NMA), whereas NMAs were rated as more aversive than NMBs. These differences between the two near-miss types were exacerbated by LDWs. Results demonstrate LDWs increase the trial-by-trial enjoyment of non-win outcomes. The motivational and hedonic effects of near-misses differed for events either side of the payline, and these differences were exaggerated by the presence of LDWs. Thus, near-misses can retain their effectiveness in complex forms of gambling that also deliver LDWs.