The El Niño/Southern Oscillation (ENSO) strongly influences the large-scale atmospheric circulation over the extratropical North Pacific during boreal winter, which has an important impact on North American winter climate. This study analyses the interdecadal variability of the ENSO teleconnection to the wintertime extratropical North Pacific, over the period 1900–2010, using a range of observationally derived datasets and an ensemble of atmospheric model simulations. The observed teleconnection strength is found to vary substantially over the 20th century. Specifically, 31-year periods in the early-century (1912–1942), mid-century (1946–1976) and the late-century (1980–2010) are identified in the observations when the ENSO teleconnection to the North Pacific circulation are found to be particularly strong, weak and strong respectively. The ENSO teleconnection to the North Pacific in the atmospheric model ensemble is weak in the mid-century period and substantially stronger in the late-century, closely following the variability in the observed ENSO-North Pacific teleconnection. In the early-century, however, the atmospheric model also exhibits a weak teleconnection to the North Pacific, unlike in observations. In a subset of the model realisations that exhibit similar ENSO-North Pacific teleconnection as in observations during the early-century period there are large differences in extratropical circulation but not in equatorial Pacific precipitation anomalies, in contrast to the late-century period. This suggests that the high correlation in the early century period is largely due to internal extratropical variability. The important implications of these results for seasonal predictability and the assessment of seasonal forecasting systems are discussed.