The Dapingian (470-467 Ma) is the earliest age during the Middle Ordovician, that occurs after the Floian (Early Ordovician), and before the Darriwilian (late Middle Ordovician).
470.0–467.3 Ma
Some of the earliest cryptospores are from Argentina which may be from land plants (Rubinstein et al. 2010)
Fossils of plant sporangia have been found in Oman with cryptospores showing concentric lamellae in their walls, similar to liverworts.