Fortunes could hardly have been more mixed for the managers in an FA Cup replay thriller which went all the way to a penalty shoot-out.
Cambridge player-boss John Taylor was devastated after his team hit back twice but lost on penalties, as he missed the vital kick himself.
Whereas Macclesfield's John Askey was able to celebrate signing a two and half year contract just before the kick-off.
It was a rollercoaster ride for him however thanks to defender Karl Munroe getting sent off a minute before half-time.
John Miles scored a great 26th minute goal to put the Silkmen in front, but Cambridge dominated after Munroe was sent off for his second bookable offence.
John Turner headed Cambridge level in the 65th minute but after Mark Venus slammed a 76th minute shot against the post the tie went to extra-time.
Matt Tipton regained the lead against the run of play for Macclesfield in the 101st minute but Adam Tann set up the penalty shoot-out with a scrambled goal in the 119h minute.
Then Macclesfield goalkeeper Steve Wilson took over as hero, saving from Taylor and Venus, before Danny Whitaker scored from the decisive spot-kick.
Said Askey: "It was a display full of character to mark me sorting out my contract and I'm looking forward to working with these players. It's a two and a half year deal.
"But discipline will be a priority because we had a player sent off in both matches against Cambridge and it gave the other lads a lot of work to do when we had been in command in the replay. " Taylor let his coach Dale Brooks do the talking as he recovered from this gruelling game.
Said Brooks: "John and the lads are devastated to go out against ten men when we had so many chances.
"But we have to look at the way we used the ball against a ten-man team. That could have been a lot better. It was a great cup-tie, but very disappointing for us."