re = /[2][0-9][0-9][0-9]\/[0-9][[0-9]\//i
str = '161 1 2015/12/17 14:52:08:44648 13668 38528 1 *** 15 5 CDF_ENTRY [Id=1] hook_MFCreateSourceResolver: Entering.
162 1 2015/12/17 14:52:08:44664 13668 38528 1 *** 15 5 CDF_ENTRY [Id=2] SourceResolverWrapper::FinalConstruct: Entering.
163 1 2015/12/17 14:52:08:44664 13668 38528 1 *** 20 5 CDF_ENTRY [Id=2] SourceResolverWrapper::FinalConstruct: Leaving. (hr=0x0)
164 1 2015/12/17 14:52:08:44665 13668 38528 1 *** 20 5 CDF_ENTRY [Id=1] hook_MFCreateSourceResolver: Leaving. (hr=0x0)
165 1 2015/12/17 14:52:08:44666 13668 38528 1 *** 15 5 CDF_ENTRY [Id=2] SourceResolverWrapper::BeginCreateObjectFromURL: Entering. '
subst = '2016/01/'
result = str.sub(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