Shuffle and repeat items in Windows Media Player
In Windows Media Player, content that you are playing appears in the List pane on the Now Playing tab. You can change the order in which the items play by turning on shuffle play, which will make items in the List pane play in a random order. You can also choose to play the items repeatedly. When you turn on repeat play, all items in the List pane will play once and then begin playing again. You can also turn on both shuffle and repeat at the same time. Note that it is not possible to shuffle or repeat DVDs.
Turning on shuffle or repeat does not change the display order in the List pane. To play only one file repeatedly, check that it is the only file displayed in the List pane.
For information about how to edit a playlist by using the Shuffle List Now command, see Create or change a regular playlist.