Maccarinelli's next fight was against the unbeaten Russian Denis Lebedev on 18 July 2009. As with the Afolabi contest the fight took place at the M.E.N. Arena on the undercard of an Amir Khan fight, this time Khan's WBA light-welterweight title challenge against Andreas Kotelnik. From the very beginning of the fight Maccarinelli struggled with the power of his opponent and by the end of the second round his right eye had swollen completely shut from the punches landed by Lebedev. In the third round Lebedev rocked Maccarinelli with an uppercut which landed cleanly through his guard and after a further barrage of unanswered punches the referee stepped in and called a stop to the fight.