As part of the Andy Murray Live event, the two players faced off on Tuesday (7 November) in what was a casual and fun encounter with the Briton donning a wig during the match while Federer played in a kilt.
At the end of it all, it was Federer who eventually emerged victorious with a 6-3, 3-6, 10-6 win over the 30-year-old.
Murray, who was playing in his first match since his quarter-final exit to Sam Querrey at Wimbledon in July, was still limping at times as he recovers from a hip problem.
Set to return in 2018 as he is confirmed for the Australian Open, Murray was offered insight by Henman, who sees scope for improvement with the three-time Grand Slam champion's serve.
"With Andy's defensive skills he's so good at changing the pace, changing the direction of the ball," Henman said, as quoted on the Express. "He needs to get more pop on his serve but that will come with more matches."
"With the hip it's been a difficult time but it's great to see them out there competing and having fun in front of an amazing audience."
Henman also reserved praise for current world number two Federer, who looked as good as ever against the 30-year-old, as he continues his career resurgence in 2018.
"There aren't too many areas of Roger's game you can attack," Henman explained. "He serves well, he's athletic, aggressive from the baseline and he can volley well."
"There's not too many holes there."