The Flash Rebirth #3 (2009) - Fifth Superman vs Barry Allen Flash race
Silver Age Flash II, Barry Allen, is brought back from the dead after 20 years and by issue #3 he's racing Superman.
I don't LOVE the artwork for this cover. And let's not even get into whether I think bringing Barry Allen back was a good idea. However, there is an awesome part during this race where Barry (Flash) and Clark (Supes) are talking and Clark mentions that as their earlier races prove, he's as fast as Barry. Barry looks at him and says that, "...those were for charity, Clark." And proceeds to turn on the juice and leave Supes in the dust. FINALLY.