If MyText is the string represented by your example, use System.Text.RegularExpressions.Regex.Matches(MyText, "\d{2}/\d{2}/\d{4}") to get all date matches.
Use System.Text.RegularExpressions.Regex.Matches(MyText, "((\d+,)+\d+)|((?=>at\s)\d+)|((?=>Total\s)\d+)") to get the amounts. This regular expression checks for numbers with commas first, and if none exist, then search for string "at " or "Total " to locate the amounts (in case the amounts do not contain a comma).
Thanks for putting efforts in studio to make this file. Appreciate it!
But, the text I gave was just an random example. The actual texts can be anything and can contain any number if dates and amounts at different places in string.