George is using "the dark ages" to refer to the time before the handicapping system was put into place. In those long-ago days, people were not equal with each other. Some had unfair advantages because they were more athletically capable or because they were smarter or because they were more physically attractive than others. Other people were disadvantaged because they were slow to learn or had poor coordination or were impaired in other areas.
In 2081, all people
were equal every which way. Nobody was smarter than anybody else. Nobody was better looking than anybody else. Nobody was stronger or quicker than anybody else.
George, and the rest of society, considered this universal equality to be a very good thing, an advancement from the past when people were not equal, but instead were "competing against everybody else." George had no interest in breaking the system enforced by the Handicapper General and her agents, even when he suffered greatly from his personal handicapping devices, because he supported the system of equalizing all persons.