I've worked in a bunch of data center/server rooms as an electrician. It always boggled the mind when they had the AC running full blast in there in January in Chicago.
It always seemed like there should be a way to bring in the cold, dry outside in during the winter, even if it had to dehumidified first. Seemed like a total waste blasting the AC.
They do use the winter air...depends on the type of cooling they employ, but either way, they take advantage of the outdoor cool air in the winter. One of the first I worked in had a chilled water system: rooftop units cool salinated water, which is piped and circulated throughout cooling coils with blowers placed where needed. The staff on site there said the system automatically turned off the cooling portion of the rooftop chillers and kept the circulation pumps on at around 40F. The center I'm in now uses outdoor air, filtered, and then pumped directly through the roof into the server rooms. These employ a larger system similar to your home AC. These cut off the cooling portion around 50F, and just pump air at that point. Rooms on the lower floors use a large system again comparable your home AC: evaporator/blower unit in the room, copper refrigerant lines to a condenser on the roof. The similarity ends there...these units have a separate compressor "circuit" in the refrigerant lines. This allows the unit to circulate the refrigerant without running the compressor when the outside air is cold enough, around 50F. Inside at the evaporator blower, the similarity ends as well; your home unit is binary...on or off. The commercial units employ variable frequency drives on the blowers and refrigerant sections...if you "wake up" the touch screen on a CRAC (Computer Room AC,) it will indicate a percentage 0-100 on both cooling and fan, which ramp up and down based on sensor readings in the room.
Data centers evaluate cost performance based on a ratio of $ of revenue in to $ of utility operating cost. The bulk of energy expended in the cooling systems are the compression of refrigerant. The operations staff at data centers do a happy dance when the weather gets like this, and early falls and late springs help their overall annual performance.