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There aren't that many games that explicitly illustrate how a faster OODA Loop/Decision Cycle can create battlefield advantage. One game company, Multiman Publishing, has several series of games that do exactly that.
Tactical Combat Series (TCS). Players in these games create what are called "OpSheets," which sketch out using military graphics orders to subordinate units. When written and issued, the actual time of implementation can vary, but forces with faster OODA Loops/Decision Cycles usually implement orders before their enemy does, especially when out of contact. Currently in-print games (and there are many out of print) include the following:
Black Wednesday: The Battle of Krasni Bor. The Spanish Blue Division attempts to fend off a much larger, but slower, Soviet force. It's a two-map game that takes a while to play.
Bloody Ridge. Can the Marines more nimble C2 keep the Japanese at bay atop Edson's Ridge in Guadalcanal in 1942? Find out in this game! One-map game that is a bit faster to complete than its sister games!
GD '42. Can the German Gross Deutschland Division hold off the massive Soviet offensive in the Luchessa Valley during OPERATION MARS? The biggest of this series of games!
Leros. The German airborne assault on this British-held island in the Aegean Sea. A fairly intricate game!
Civil War Brigade Series (CWB). Players in these games issue written orders to subordinate units, which have variable times for implementation. This series more than any other explains the craziness of Civil War battles.
April's Harvest. The Battle of Shiloh. One of the most frustrating games in the series for both the Union and Confederate players as the close terrain serious interferes with command and control.
Champion Hill. The last chance for the defenders of Vicksburg to break out from Grant's impending encirclement and siege.
In Their Quiet Fields II. The battle of Sharpsburg/Antietam Creek. Witness Robert E. Lee's tight OODA Loop versus the far looser one of Union Major General McClellan.
Napoleonic Brigade Series (NBS). As with the CWB, players issue orders to subordinate formations, but all will likely not go according to plan!
Marengo. A very near run thing for Napoleon, who is only rescued by the timely arrival of Desaix.
Talavera. Key battle for Napoleon in Spain, one the French will win but not decisively enough! Includes the Battle of Vimiermo as a bonus!
Operation Mercury: The Invasion of Crete by MMP
Designed by Joe Chacon, a retired Army lieutenant colonel, this is perhaps the best game within the Grand Tactical Series (GTS) of games in demonstrating German OODA Loop superiority. The German airborne division is scattered all over the north coast of Crete (lacking a Schwerpunkt initially--nearly fatal for them)--and takes very heavy losses in the initial drops that land close to their objectives. The companies then have to find their comrades to coalesce into functioning larger formations and quickly attack against the more lethargic polyglot Commonwealth troops that outnumber them. to seize an airfield so that reinforcements can arrive.
The game does this by rating formations in terms of Command and Dispatch Points which are at the core of the OODA Loop model. Faster formations have a high chance or receiving them from turn to turn. Dispatch Points are spent to purchase activation chits--more for the current turn, less for the following turn--that are all placed in a mug. Players pick out these chits to create a random sequence of play. Dispatch Points represent plans/orders reflecting staff work. Command Points enable subordinate commanders to act on units within their command range--the more points a player has, the more he can do. These can be spent on units that just acted on their Dispatches, accelerating their tempo.
The primary disadvantages of the games in this series is that most of them are big--half of them very, very big. While there are numerous small scenarios, they easily fall outside the wargame budget unless a number of gamers pool their funds to make a purchase for a club. Operation Mercury is the best of them all and is still in print as of this writing. For detailed descriptions of the system and the other games in the GTS series, see these discussions on the following games:
No Question of Surrender: The Battle for Bir Hacheim (the smallest of all of them, but the Free French brigade is stuck in its defensive box)
The Greatest Day: Sword, Gold, and Juno Beaches (I've not had a chance to play it yet as it's the biggest of all in the series but has oodles of smaller scenarios)