IWC created a “Spezialuhr für Flieger” (“Special Watch for Pilots”) in 1936 with clean black dial, large hands, and luminous numerals. Although the 36 mm case was fairly large for the time, pilots preferred an even larger dial and crown for extra visibility in the cockpit. In 1940, IWC responded with an official product, the prototypical “Big Pilot's watch”. Created for the German Air Force, it had a massive 55 mm diameter case. The dial featured a luminous triangle at 12 flanked by two dots, plain numerals, and large luminous sword hands. Another essential element was a massive cone-shaped crown, allowing the watch to be operated while wearing gloves.
By the end of the 1990s, the Mark XV and Pilot's Watch Chronograph had become signature models for IWC. Watch case sizes were growing rapidly, and consumers were responding to “heritage” models that recalled the past. In 2002 IWC resurrected the oversized “Grosse Fliegeruhr” as the Big Pilot, Ref. 5002. It used the new in-house automatic Cal. 5011, which used the company's trademark Pellaton winding system and boasted a seven-day power reserve. This was refreshed in 2006 with the updated Cal. 51110 as Ref. 5004.
Also in 2006, IWC released a special limited-edition Big Pilot Perpetual Calendar, Ref. 5026 in a 46 mm case. A Top Gun Perpetual Calendar, Ref. 5029 followed in 2012 with a larger 48 mm ceramic case, and the slightly different 46 mm Ref. 5028 arrived in 2013 with a “single” moon phase indicator instead of the double. These watches shared a similar movement, Cal. 51612, 51613, or 51614, a descendent of the first modern in-house IWC movement, Cal. 5000. This was an eight day movement with Pellaton automatic winding but a single barrel which negatively impacted isochronosm when fully wound or unwound.
In 2016, IWC introduced a new double barrel seven day movement for the perpetual calendar series. Cal. 52610 was improved in many other respects as well, being a new design benefiting from two decades of experience. It beats at 28,800 A/h. That same year, IWC began renaming the Big Pilot line to match the Pilot's Watch. Thus, the new Ref. 5038 was named Big Pilot's Watch Perpetual Calendar.
Two models of Ref. 5038 have been released, both in limited editions “Antoine de Saint Exupéry” features a brown color scheme while “A Tribute to the 1st IWC Pilot's Watch” is grey and with a blue strap. Both feature a single moon phase indicator at 12 00.
Spitfire Bronze, Ref. 5036 was introduced at SIHH in 2019. Part of the new IWC Pilot's Watch Spitfire collection, the Spitfire Perpetual is a limited edition of 250 pieces. It features a green dial and bronze case with a double moon phase indicator thanks to Cal. 52615.
Another model introduced at SIHH in 2019 is the Rodeo Drive Ref. 50300. This uses a black ceramic case slightly larger at 46.5 mm, reminiscent of the Top Gun models, and has a blue dial like the Little Prince watches. It also uses Cal. 52615 and has a double moon phase indicator. The Rodeo Drive is the first unlimited model of the new Perpetual Calendar.