We document the first confirmed cases of polygyny and double brooding in the Eastern Wood-Pewee (Contopus virens). During an intensive study of the effects of shelterwood harvesting on canopy-nesting songbirds in southeastern Ohio, 2007–2010, we color-banded 79 Eastern Wood-Pewees and monitored 237 pewee nests. In 2007, we confirmed a color-banded male provisioning at two concurrently active nests; the male was polygynous in at least two consecutive years. In 2009, we observed an unbanded female feeding fledglings and subsequently shaping a nest from which young had recently fledged; the female successfully fledged two broods from the same nest. In addition to confirmed observations, we identified several other probable cases of polygyny and double brooding. In our upland oak system, we estimated rates of polygyny from 6–22% with the greatest occurrence of polygyny during a dry spring in 2007; rates of double brooding may have been as high as 6–12%. Males appeared to benefit from polygyny, because males paired with two females fledged twice as many young compared to monogamous males, without any apparent negative effect on return rate. Overall, we did not find negative effects on reproductive success for females paired with polygynous males, although we were not able to consistently differentiate between primary and secondary females. Polygyny appeared to be related to either territory quality and/or male quality with nests of polygynous males located in preferred nest sites while provisioning rates were greater at polygynous compared to monogamous nests. In addition, we only found experienced males paired with two females. Both males and females benefited from double brooding, fledging twice as many young as single brooded pairs, but in our system double brooding appeared to be limited by high levels of nest predation early in the breeding season.