U's legend Karl Duguid took charge of Colchester United for the first time in their Essex Senior Cup quarter-final at AFC Hornchurch.
The 34-year-old, who has made more than 450 league and cup appearances for the U's, has been offered a player-coach role at the club.
And he was given the chance to put his coaching skills to the test when he led Colchester into battle, against the Urchins.
U's boss Joe Dunne said: “Karl took the team against Hornchurch and it was a great baptism of fire for him.
“I had a similar experience when I was starting out in coaching and it’s invaluable.
“It was a case of him going in at the deep end but he had good support from Richard Hall."
Dunne said the tie was a useful game for the U's, despite them eventually falling to a 4-3 defeat.
“The likes of Alex Gilbey and Andy Bond both got a valuable 90 minutes," said the U's boss.
“George Porter also played as did Jack Compton and we took him off as a precautionary measure.
“Jack picked up a knock against Doncaster - it’s nothing too serious and we wanted to get him some more game time."
See the Daily Gazette for all of the latest Colchester United news.