Como iterar padrão por outro?

Question

Eu tenho a saída abaixo. Eu tento iterar as mesmas vezes que o Date and Time: Month Day Year HH:MM:SS para cada Application n.n string o encontrou.

===================================================================================
Application Server: Server
Date and Time: Month Day Year HH:MM:SS
Server IP Address: 111.111.111

Program                 Total in use
Application1                2
Application2                2
Sub Application1            0
Sub Application2            0
Application     n.n     user     user     1.11.11.11     11:11
Application2     n.n     user     user     1.11.11.11     11:11

Syntax error bla bla bla    

===================================================================================

Exemplo, se eu for minha saída:

Application     n.n
Application     n.n
Application     n.n
Application     n.n

Eu quero outra saída será como:

Date and Time: Day Year HH:MM:SS
Date and Time: Day Year HH:MM:SS
Date and Time: Day Year HH:MM:SS
Date and Time: Day Year HH:MM:SS