Yes, Skedi syncs with Microsoft Outlook via iTunes or over the internet through Outlook Hotmail Connector We recommend Outlook Hotmail Connector because you don't have sync your device with your computer. Note: If you are already using Microsoft Exchange at work, these steps are unnecessary. Your iPhone syncs directly with your Microsoft Exchange account.
Sync with Outlook Hotmail Connector: Overview, Download, and System Requirements
Syncing with iTunes: Synchronize Outlook and Apple iPhone or iPod touch calendars