Amy,

If you step through your code you will see that you first insert "apples"
before the bookmark range and then you insert oranges before the bookmark
range which is before apples.

You could build a string first and then just insert it at the end of the
code:

Private Sub CommandButton1_Click()
Dim i As Long
Dim myString As String
For i = 1 To Team.ListCount
   '..and check whether each is selected
   If Team.Selected(i - 1) Then
       ' If selected, display item in msgbox
        myString = myString + Team.List(i - 1) & " "
   End If
Next
ActiveDocument.Bookmarks("Team").Range.InsertBefore myString
Me.Hide
End Sub

Or just process the ListCount is reverse order:

Private Sub CommandButton1_Click()
Dim i As Long
For i = Team.ListCount To 1 Step -1
   '..and check whether each is selected
   If Team.Selected(i - 1) Then
       ' If selected, display item in msgbox
       ActiveDocument.Bookmarks("Team").Range.InsertBefore Team.List(i - 1)
& " "
   End If
Next
Me.Hide
End Sub