On the Contests tab, add the classics — Closest to the Pin, Longest Drive, Skins, Putting, Hole-in-One. For each you can set the hole, the prize, and the sponsor. When you know the winner, pick them and enter the result (e.g., "12 ft" or "312 yds"). A contest shows on your leaderboard and TV board once it's marked awarded (i.e., once you've selected a winner).
Possible hole-in-one. If a group enters a score of 1 on any hole, Redswing flags a possible hole-in-one on the Scoring page. Check with the group, then click Confirm ace or Dismiss. There is no field-wide hole-in-one text you can turn on today. See Hole-in-one alerts.