re = /^StartWord\R+\K.*?\R(?=\R*^StopWord\R)/m
str = 'Delete this text De l e te this text
StartWord
Apples Oranges
Pears Grapes
StopWord
Delete this text Delete this text
StartWord
Peas Carrots
Peas Carrots
StopWord
Delete this text Delete this text
'
subst = ''
result = str.gsub(re, subst)
# Print the result of the substitution
puts result
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for Ruby, please visit: http://ruby-doc.org/core-2.2.0/Regexp.html