As a player Tim Henman frequently had his heart broken by Lleyton Hewitt, but now a small measure of revenge could be served cold in the ATP Cup.
Well over a decade on from their on-court rivalry the two men find themselves as opposing captains in the quarter finals of the inaugural team competition, with Henman once again finding himself cast as the underdog.
Late on Wednesday evening UK time, Great Britain will take on Australia in a quasi-Ashes clash at the £12million event, after another night of early hours drama saw them pass through to the last eight as group winners.
Tim Henman (left) and Lleyton Hewitt (right, pictured in 2007) had a rivalry as players
Henman is now ready to come up against his old adversary as part of the ATP Cup tournament
Hewitt is captain for Team Australia while Henman is in charge of Team Great Britain
At well past midnight Belgium won a deciding tiebreak in the deciding doubles rubber to beat Bulgaria 2-1. That was, mathematically, enough to seal GB's passage after they had earlier defeated Moldova 3-0, with the succession of straight sets victories boosting their win/loss ratio sufficiently.
Now for a quarter final that will delight the organisers and is sure to pack out the 12,000-seat Ken Rosewall Arena.
Hewitt and the likes of Nick Kyrgios are hotfooting it down from Brisbane, and they will have had less than a day to get used to the venue where Britain have been ensconced for more than a week.
Nick Kyrgios is in inspired form for hosts Australia and is a big weapon in their team arsenal
Dan Evans is GB's highest-ranked player and Henman is looking to coax the best from him
Coming up against Hewitt will bring back some unwelcome memories for Henman, who always found the blonde baseliner's game difficult to deal with.
He lost nine matches out of 10 against the Aussie scrapper, most painfully in the 2002 Wimbledon final and in two finals of the pre-SW19 grass court event at Queen's Club, now the Fever Tree Championships.
This is the match Henman has been hoping for since the event started: 'Obviously I have a lot of history with Lleyton, and everyone knows their team well,' said the GB captain. 'I feel like there has been a great spirit in our team, I have certainly kept an eye on the other groups and what's been going on. It will be a lot of fun.'
It looks a tall order for the GB team,