Mercedes chief strategist James Vowles described it as 'heartbreaking' Mercedes was unable to claim a Formula 1 Grand Prix victory with Michael Schumacher.
The seven-time champion drove for Mercedes upon its return to the sport in 2010 but scored just one podium in his three years with the team.
A highlight of Schumacher's time with Mercedes came when the German set the fastest time in qualifying for the 2012 Monaco Grand Prix.
However, a five-place grid penalty carried over from the preceding race in Spain relegated Schumacher to sixth on the grid, robbing him of the chance to score a fairytale victory.
Recounting the weekend, Vowles told the Beyond the Grid Podcast: “I was over the moon and I think it was one of the best laps he’d probably ever done in his life.
"But I was heartbroken, truly heartbroken for him that this is a guy that we all wanted to win a race, because he deserved it frankly, and he put so much effort into the team and so much of his life into the team that it was payback for him and that was his opportunity through the year.
"I was heartbroken with the fact that that one race was where he dropped back. I felt for him, I still feel now... he didn’t get all the results that he deserved give the amount he was putting in the team.”
Three races before Monaco, at the Chinese Grand Prix, Nico Rosberg had scored Mercedes' first win since its return but the vast majority of the team's success came after Schumacher's 2012 retirement.
Mercedes sporting director Ron Meadows added: “Given how he helped us improve, I think certainly my biggest regret was not seeing Michael win a race for us because he was a different level of driver we’d ever worked with at that point.
“I really believe we all wanted him to win. It didn’t happen. A couple of years later we couldn’t stop winning and he deserves some of that because the reason we’re winning today, a lot was down to him because he made us better.”
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