First, one of their defensive mainstays of last season, Markus Babbel, was diagnosed as suffering with the rare Guillain-Barre syndrome.
At half-time against Bolton on August 28, the German international asked Gerard Houllier if he could be withdrawn. A check found that his immune system was low, but he resumed training after two months.
His nervous system was then struck and a German specialist discovered the illness.
Then, at half-time on Saturday October 13, manager Houllier was rushed to hospital complaining of chest pains and later went through 11 hours of heart surgery and has only recently returned to the dug-out.
With key player and manager both suffering major health scares, it has certainly been a testing campaign for the Anfield staff.
"It has been," agreed Jamie. "It's not been an easy season for Liverpool. But they've got that resillience and strength of character to battle through it.
"Phil Thompson did a great job when Gerard Houllier wasn't there and the club, from top to bottom, is a very strong unit.
"I find it amazing how they stay so together really."
Happily, with now Houllier restored to full working order, Babbel too is hoping for a emotional five-minute run-out in the final game of the season before preparing for the new campaign.
"It was all unbelieveable," added Jamie. "But now Markus is going to be back for next season with a bit of luck. I like Markus and wish him all the best."
Jamie Redknapp has praised the remarkable 'resilience and strength' of the Liverpool team in battling through what has been a traumatic season for them.