Their relationship is likely to survive 90 minutes in Perth, then, where Cregg will today play in St Johnstone's midfield in a match with Inverness Caledonian Thistle.
Hughes is now manager of the Highland side, having previously spent time out of the game after an ill-fated spell as manager of Hartlepool United. He had to wait patiently to be called back into football but was not allowed to feel disconnected. Cregg was on the phone every now and then just to catch up.
It wold seem likely that the pair will find time to catch up again at McDiarmid Park this afternoon. "I'd class him a friend and I class him a very good man, and I'm glad he is back in football," said Cregg, who played under Hughes at both Falkirk and Hibernian, where he was released by his erstwhile manager after just one season.
"He's a very good guy, but that goes out of the window on Saturday. He is very likeable and very fair and honest with you. I speak to him the odd time, just wishing him luck. When he was out of football I would see how he was. He was very good to me over the years, so that's the way it is."
Their respective clubs have grown closer in the SPFL Premiership table too, with St Johnstone just six points behind their visitors today. "We finished third last season and we definitely want to finish in the top six again this season and Saturday is a great chance to close the gap on Inverness," Cregg added.
The attention of Inverness may lie elsewhere this season. The club have slipped out of the running for second place but will be keen to get back on their feet again ahead of a Scottish League Cup final against Aberdeen next month. It is a fixture which has given new significance to a relatively less enthralling trip to Perth.
"The next two or three weeks will probably be the most exciting the club has ever had," said Aaron Doran, the Inverness winger. "We're in the quarter-finals of the Scottish Cup against Dundee United and then we play Aberdeen in the League Cup final. That is what you are a footballer for, playing these kind of games."
Now in his third full season at Inverness, Doran is able to retrace his side's progress. "Two or three years ago, playing under Terry Butcher, we were at this stage still fighting to get out of the relegation zone," he added. "Look at us now - still in both cups and going well in the league.
"There's so much to play for and that can only help us in Perth because every single player wants to win the right to be involved in these kind of matches."