Cabernet Sauvignon (CS) and Cabernet franc (CF) vines were subjected to two crop levels (full, half) and three harvest dates (earliest to latest; T0, T1, T2) over two vintages. Wines were analyzed for anthocyanins, phenolics, and proanthocyanidins. Crop level increased CS hue (2011–2012), increased CS pH and reduced CS color intensity (2012), and reduced CF hue (2012). Harvest date had a greater effect than crop level, with many treatment interactions. Half crop (2011) increased three CS anthocyanins plus procyanidin B. Extended harvest increased eight compounds. Quercetin and ( )-catechin decreased in T1. Crop reduction (2012) increased malvidin-3-coumarylglucoside and ( )-catechin, but decreased petunidin and delphinidin-3-coumarylglucoside. Harvest date (2012) impacted all but two compounds, with the highest anthocyanin concentrations in T1 wines. Gallic acid, ( )-catechin and resveratrol increased with harvest date, while three phenols decreased. Half crop (2011) increased CF peonidin. Extended harvest increased four phenols while three others decreased. Crop reduction (2012) increased delphinidin-3-acetylglucoside, cyanidin-3-coumarylglucoside and caffeic acid; (-)-epicatechin and p-coumaric acid decreased. Several anthocyanins and phenols decreased between T0 and T2, nine of 13 anthocyanins decreased between T0 and T1, while others decreased from T1 to T2. Gallic acid and ( )-catechin increased with harvest date; (-)-epicatechin, p-coumaric acid, quercetin, and resveratrol decreased.