Mesoscale eddies in the south west Pacific region are prominent ocean features that represent distinctive environments for phytoplankton. Here, we examine the seasonal plankton dynamics associated with averaged cyclonic and anticyclonic eddies (CE and ACE, respectively) off eastern Australia. We do this through building seasonal climatologies of mixed layer depth (MLD) and surface chlorophyll-a for both CE and ACE by combining remotely sensed sea surface height (TOPEX/Poseidon, Envisat, Jason-1, and OSTM/Jason-2), remotely sensed ocean color (GlobColour) and in situ profiles of temperature, salinity and pressure from Argo floats. Using the CE and ACE seasonal climatologies, we assimilate the surface chlorophyll-a data into both a single (WOMBAT), and multi-phytoplankton class (EMS) biogeochemical model to investigate the level of complexity required to simulate the phytoplankton chlorophyll-a. For the two eddy types, the data assimilation showed both biogeochemical models only needed one set of parameters to represent phytoplankton but needed different parameters for zooplankton. To assess the simulated phytoplankton behavior we compared EMS model simulations with a ship-based experiment that involved incubating a winter phytoplankton community sampled from below the mixed layer under ambient and two higher light intensities with and without nutrient enrichment. By the end of the 5-day field experiment, large diatom abundance was four times greater in all treatments compared to the initial community, with a corresponding decline in pico-cyanobacteria. The experimental results were consistent with the simulated behavior in CE and ACE, where the seasonal deepening of the mixed layer during winter produced a rapid increase in large phytoplankton. Our model simulations suggest that CE off East Australia are not only characterized by a higher chlorophyll-a concentration compared to ACE, but also by a higher concentration of large phytoplankton (i.e., diatoms) due to the shallower CE mixed layer. The model simulations also suggest the zooplankton community is different in the two eddy types and this behavior needs further investigation.