A major obstacle to understanding how expenditure varies amongst people who gamble is the difficulty of obtaining accurate expenditure data from individual gamblers. To overcome the shortcomings of retrospective self-reports, this study used a prospective ecological momentary assessment (EMA) design to capture these data every 24/48 hours. It aimed to examine 1) demographic, psychological, behavioural and contextual characteristics of high-spending sports and race bettors, and 2) the relationship between betting outlay and problem gambling severity. A baseline survey was completed by 320 regular sports bettors and 402 regular race bettors, followed by 15 EMA surveys over three non-consecutive weeks. Higher spending bettors were more likely to: be male, place more of their bets online, have higher disposable incomes, have commenced betting at a younger age, have more accounts with betting operators, and bet when affected by alcohol. The analyses confirmed the strong link between problem gambling severity and financial outlay on betting. Regular sports bettors experiencing gambling problems spent four times more, and those at moderate-risk spent three times more, than their non-problem gambling counterparts. Regular race bettors experiencing gambling problems spent three times more, and those at moderate-risk spent twice as much, as the non-problem gambling race bettors. These results suggest that regulatory and other initiatives that help bettors to limit or reduce their financial outlay on betting should be central to harm minimisation efforts, in order to reduce the growing number of bettors experiencing gambling problems and harm.