Today is the 66th anniversary of the Raid on St. Nazaire by British commandos.
The raid was noteworthy for being seaborne, led by a former U.S. lend-lease destroyer, the HMS Campbelltown, modified for the raid to resemble a German craft. The main objective of the raid was to disable the Normandie dock, the only dry dock along the coast of France big enough to hold the German battleship Tirpitz. The hope was that eliminating the only facility that could repair the battleship would deter the Germans from sending it on an Atlantic raid.
Led by the explosive-laden Campbelltown, which was to ram the dock, a force of several hundred commandos aboard a bunch of light craft were also to do as much extra damage as they could. In 1987 Avalon Hill published the solitaire game Raid on St. Nazaire which depicts the raid, rather well, too.
I'm surprised that there aren't more solitaire wargames on raiding operations. One of the hardest aspects of warfare to capture in wargames is the factor of surprise. In real life battles can erupt that one side had no idea was coming. Naturally the players in a wargame inherently know something is up, so real surprise is hard to achieve and usually the designer has to resort to various restrictions imposed by the rules.
Likewise, one of the factors that raiders seek to exploit is the disorganized response of the surprised defenders. In fact, in a rear area it's quite likely that there is no overall commander or chain of command to oversee the battle, so the defenders don't even have the means to act in concert.
A solitaire game like Raid on St. Nazaire can build this in. The only "organized" side is the one represented by the player, who can apply his planning to direct the actions of his troops, subject to the usual restrictions of time, space and military realities. The game system can capture the disjointed, unorganized response by the defenders. While outnumbering the raiders, the defenders don't have the means to bring that advantage to bear in the short time the raiders will give them.