Agricultural phosphorus (P) management is a research and policy issue due to P loss from fields and water quality degradation. Better information is needed on the risk of P loss from dairy manure applied in winter or when runoff is imminent. We used the SurPhos computer model and 108 site–years of weather and runoff data to assess the impact of these two practices on dissolved P loss. Model results showed that winter manure application can increase P loss by 2.5 to 3.6 times compared with non-winter applications, with the amount increasing as the average runoff from a field increases. Increased P loss is true for manure applied any time from late November through early March, with a maximum P loss from application in late January and early February. Shifting manure application to fields with less runoff can reduce P loss by 3.4 to 7.5 times. Delaying manure application when runoff is imminent can reduce P loss any time of the year, and sometimes quite significantly, but the number of times that application delays will reduce P loss is limited to only 3 to 9% of possible spreading days, and average P loss may be reduced by only 15% for winter-applied manure and 6% for non-winter-applied manure. Overall, long-term strategies of shifting manure applications to low runoff seasons and fields can potentially reduce dissolved P loss in runoff much more compared with near-term, tactical application decisions of avoiding manure application when runoff is imminent.