The 1984 FA Cup final is six minutes into the second half. Watford trail 1-0 when Everton's Trevor Steven delivers a hanging cross. Sherwood gathers, but a second later a thrust of Andy Gray's forehead dislodges the ball from his grasp to send it spinning into the net. Shades of Lofthouse versus Gregg, and, just as in '58, the goal is given.
These days, Gray peppers television screens with arrows and squiggles as a hi-tech Hansen. Sherwood is also concerned with assessing angles and off-the-ball movement, but with an important difference. A month before he hits 44, the Yorkshireman is still there to be shot at.
When Saturday comes, the man best known for losing out to a challenge that would not have been out of place at Wakefield Trinity will be guarding Gainsborough Trinity's goal in a first-round derby at Lincoln City. A bunch of part-timers lying ninth in the UniBond League should not have a hope away to a side fourth in the Third Division, yet Sherwood is due an even break from this competition.
"I look back on Wembley with a mixture of pride and sadness," he said. "It was an achievement for Watford just to get there, so soon after Graham Taylor brought us up from the Fourth Division. We also had the youngest defence ever to play in the final. I was the veteran even then!
"But I've got the game on video and the view from behind the goal shows clearly that Andy didn't head the ball cleanly. I accept that he was only doing his job and we've had a laugh about it since, though the papers weren't too kind to me the next day.
"It was disappointing, not just because we lost but because one poor decision killed the game when there was still a long way to go. We were positive we could still get into it, but it died a death after that."
Three years later, fate seemed ready to make amends. An injury to Tony Coton, by now Watford's No 1 keeper, brought Sherwood back into the side as they advanced towards the twin towers. However, in the build-up to the semi-final against Tottenham he dislocated a finger in training.
"The hospital put it back in and I believed I was fit. Unfortunately, the manager [Graham Taylor] felt it wasn't worth the risk - we had 10 League games left and we'd slid down the table - which I didn't agree with.
"Instead, he played the secretary's son, Gary Plumley, who'd retired and was running a wine bar. We lost 4-1, so it was another case of what might have been. But I can't speak highly enough of Graham Taylor. It was fantastic to be part of Watford's rise under him."
The son of an ex-Huddersfield keeper and brother of John Sherwood, the former Olympic hurdler, he began with Chelsea where his team-mates included Charlie Cooke, Ray Wilkins and "Chopper" Harris. During a decade at Watford he went on loan to Brighton, Millwall and Brentford, later joining Grimsby and Northampton. He was still turning out for Lincoln, of all clubs, two years ago.
There were also spells at Immingham, Stalybridge and Gateshead before he signed for Ernie Moss, Gainsborough's manager and one of the few men in football more widely travelled than him. Sherwood's job as a financial adviser for an insurance company means he is not always able to train. He has, none the less, made a vital contribution to a Cup run which started in the cricket season.
Moss takes up the story. "There was one particular save in the fourth qualifying round against Halifax, who were unbeaten and top of the Vauxhall Conference. We'd equalised to make it 1-1 when a ricochet fell to to their leading scorer, [Geoff] Horsfield, 10 yards out. He struck it superbly, but Steve made a brilliant reaction stop. Within a few minutes we'd got the winner."
Knocking out Halifax was, said Sherwood, "as satisfying as any win in my career". Really? "Absolutely. Most of the younger lads have never been to the first round and the look on their faces said it all," he explained. "We had champagne in the dressing-room and crates of lager - it was a massive thing for the club."
Why does he continue to put himself in the firing line?
"Because playing gives me an incredible buzz," he replied, almost affronted.
"I do feel the aches and strains the day after a game more than I used to, and I know I'm not going to get any better at my age. But experience is crucial in my position and I like to think mine has helped Gainsborough."
They are likely to need it at Sincil Bank. A century ago, in their inaugural Football League campaign, Trinity routed Lincoln 7-0 and later beat them 5-1 in the Cup. They also won 3-0 in a friendly last summer, though Sherwood and Moss know that history, ancient or modern, will have no bearing on the outcome.
Delving further into his catalogue of Cup disappointments for an example of what Gainsborough might achieve, Sherwood recalled Northampton succumbing at home to Bromsgrove. "It's not a nice experience for a full-time pro to lose to non-League opposition. You feel humiliated."
When Watford were shaking up the elite with their route-one football, Sherwood's booming clearances launched many an attack. He even scored at Coventry but can no longer kick so far. "If I could," he reflected, "I'd probably be playing for Lincoln rather than Gainsborough, given John Beck's reputation for the long-ball game."
The humour, like the hunger, has clearly survived that Gray day at Wembley.