Andy, 30, from Helston Crescent, Monk Bretton, will kick things off with a 127-mile bike ride along the canal from Liverpool to Leeds to raise funds for Sheffield Hospitals' Charity, where his wife Jenny, 31, is undergoing treatment for Hodgkins lymphoma.
In October Andy will be amongst a group of 33 people who will attempt to run the full 35 mile length of the Wakefield Wheel Cycle Route.
Andy, who works as a sport development manager at Rossington School in Doncaster, then plans to top it off by running two marathons - one in Manchester, one in Chicago.
He said: "Jenny has been battling Hodgkins lymphoma for the last three years. Initially, she was treated at Barnsley Hospital and wasgiven the all clear in 2013. However, we got the dreadful news in June that it had come back and that she needed to be treated at the Royal Hallamshire Hospital.
"Jenny is currently undergoing that treatment and is doing well. I'd like to raise as much money as I can as a thank you to both Barnsley Hospital chemo ward and the hospital in Sheffield where they have really looked after Jen."
Log onto www.justgiving.com/wakefieldwolfpackforjen if you would like to support the challenges.