The Naples outfit have won all four of their competitive fixtures under the Spaniard, a run which has seen them top Serie A and open their UEFA Champions League campaign with a victory over last season's runners-up Borussia Dortmund.
Milan, meanwhile, have endured something of a mixed start to 2013-14, posting one defeat, one draw and one loss in their first three league fixtures while proving unconvincing in Europe.
Massimiliano Allegri's men came through a potentially testing Champions League play-off against PSV Eindhoven, but needed an 82nd-minute own goal to make the breakthrough before defeating Celtic 2-0 in their first group game.
That famous victory came in the season prior to Maradona leading Napoli to the Scudetto, and Benitez will be keen for his team to lay down a similar marker in terms of their title hopes with a historic win.
His chances of overseeing such a famous victory are surely helped by Milan's injury list, which includes Riccardo Montolivo, Stephan El Shaarawy, Kaka (all thigh), Daniele Bonera and Mattia De Sciglio (both knee).
