Damaging winds, associated with a variety of weather phenomena, are frequently experienced in New Zealand. Observations and modelling of two recent extreme wind events; the Taranaki tornado outbreak of July 2007, and the Greymouth down-slope easterly wind storm of July 2008 are described in detail here. Post-event engineering damage surveys, rare for New Zealand, were done for these storms and the results are summarized here. Finally, the issue of sampling extreme wind events is raised and the need to include detailed numerical modelling analysis to understand wind gust climatologies at observing sites and extending these to wider regions is discussed.