On Saturday, Sherwood heads back to Spurs, this time in the away dugout as his struggling Villa side battle to avoid Premier League relegation that would end 27 seasons in the top flight.
Sherwood is likely to get something of a mixed reception from the White Hart Lane crowd despite spending a total of 10 years at Spurs in roles as a player, coach, youth development guru and finally head coach.
One fan in particular, however, might be pleased to welcome him back as the opposition's boss.
During what proved to be his last match in charge against Villa, Sherwood called a fan from the stands, gave him his trademark gilet, and beckoned him to take his place in the dugout alongside assistants Les Ferdinand and Steffen Freund.
At his post-match press conference a laughing Sherwood said the fan regularly gave him advice on what he was doing wrong.
"That guy's an expert, seriously," he joked.
"Every week he tells me what to do. So I gave him the opportunity to do the job. He bottled it at first but then he swallowed it. It was just good banter."
The banter was not quite so jolly between Sherwood and his chairman Daniel Levy, who gave him an 18-month contract in December 2013 but sacked him last May after Spurs finished sixth and missed out on the Champions League.
Sherwood had been brutally honest about his players two months earlier following a 4-0 defeat at Chelsea and likened himself to a supply teacher towards the end of his reign.
"I am doing this job with a lot of uncertainty around my future," Sherwood said a few days before being sacked.
"If you have a supply teacher who comes into your school, sometimes they are not treated with the respect that a headmaster is."
Sherwood has already had one big reunion this week with Chris Ramsey, his former assistant at Spurs, who is now the Queens Park Rangers manager.
The two side's drew 3-3 on Tuesday, with a point doing little to ease either team's relegation fears as Villa remain 16th on 29 points, three more than 18th-placed QPR.
(Reporting by Mike Collett; editing by Michael Hann)
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