It is one of those "not-a-lot-of-people-know-that" facts that Smith was born, 58 years ago, three days after Cliff Richard. But while the Peter Pan of pro-celebrity tennis finally got to play centre court at Wimbledon, albeit to serenade the crowd during a deluge, Derby County's affable, estimable manager has never taken centre stage at Wembley in the FA Cup final.
"You'd have to be a cold fish not to imagine yourself lifting the Cup," Smith chuckles in a deep, sandpaper South Yorkshire voice that makes Brian Blessed sound like a castrato. "You think about it when you're driving to watch a night match at Peterborough or somewhere. Football's a dream factory, and that's one of mine."
His affection for the world's first and finest knockout tourney has been conspicuously unrequited down the years. To reach this season's last four, for example, Derby must come through a fourth consecutive away draw, today's visit to the holders, Arsenal.
Highbury, the setting for the first half of a semi-final saga in 1992 which ended unluckily for Smith at Villa Park, looms large among his Cup memories. Yet they also include tales of long-ago games at god-forsaken grounds and of sepia-tinted ties in a bygone age.
His earliest recollection of the Wembley trail is of squeezing into Hillsborough's now- infamous Leppings Lane end in 1953, where small boys were passed over heads to the front. With 60,000 others he saw Blackpool, complete with Stanley Matthews, take their first step towards winning the trophy. Disappointed as he was, the 12-year-old Sheffield Wednesday supporter was smitten.
Smith developed into a midfielder good enough to be considered for England Under-18s. His trial match, at Corby, was snowed off after 25 minutes, and when it was restaged the selectors gave his place to one Norbert Stiles.
Talking of whom, mention 1966 to Smith and he thinks not of the toothless, dancing Nobby or the Russian linesmen but of Wednesday's run to the FA Cup final. He cheered them to victory over Chelsea in the semi-final at Villa Park, and drove a brash Huddersfield apprentice named Frank Worthington to Wembley, where the Owls somehow lost to Everton after leading 2-0.
His own Cup debut had come four years earlier, after he joined Aldershot from Sheffield United on a free transfer, and ended in defeat at Port Vale. The following year, however, he helped the Fourth Division side knock out Aston Villa, from the top flight. "For several years running, the club who beat Villa had gone on to win it, so we were thinking it might be us," Smith says. "Then we lost at Swindon."
After joining Halifax, he was in the team which scraped a draw on a tricky surface at Bishop Auckland. Smith heard the amateurs' manager remark: "It'll be great at their place because it's a good pitch and we'll beat them." The speaker was Lawrie McMenemy, and it is as well that his reaction to a 7-0 replay defeat is lost in the mists of time.
Switching to Lincoln, where Derby's new coach Ray Harford was a colleague, Smith was in the side drawn away to Birmingham. The manager, Ron Gray, took them to Blackpool for five days before the match. Smith remembers an old Southampton player telling him how they had stayed in the resort prior to a tie at Manchester City, got drunk every night and won 5-1. Lincoln's stay contained only some of the same features.
"We went to the pictures first night and a few of the lads were 15 minutes late getting back. The gaffer went mad. He called a meeting and said: `Right, we're going home.' We talked him out of it but the next night was New Year's Eve. He told us: `You can't have a drink but we'll all have a glass of champagne at midnight.'
"We saw these people in dicky-bows arriving at the hotel and we thought: `Bugger this.' We went to my room and got stuck into some sherry. At 12 o'clock, there were five of us, arms linked, singing `Auld Lang Syne'!" Lincoln lost 2-1.
Taking his first managerial post in 1968, with Boston United of the Northern Premier League, he continued to play, as well as acting as secretary and commercial manager. The night before one tie, against Portsmouth, found him putting stickers on the stand seats, though an earlier round is burned more strongly into his memory.
Boston travelled to Ellesmere Port on Merseyside. One of the home side, "a right hard bastard" who had best remain nameless, repeatedly threatened their players. "It was a very exposed ground and the coldest, most Arctic weather I ever played in. We went one up but they had the wind behind them in the second half.
"The game was going on at one end and we looked round to see this head- case standing over one of our forwards. He'd nutted him. After he was sent off, they kept on to the referee to abandon the match. Afterwards the ref came into our bath and I asked him: `Why didn't you stop it, then?' He looked at me and said: `I ain't fucking coming back here!'"
Smith's break in League management came with Colchester. In 1974-75, having hung up his boots, he led them to the last eight of the League Cup, but even then success in the FA version proved more elusive. "We were drawn away to Leatherhead or Bishop's Stortford so I went to their replay. It was a terrible game and I said to our coach, Bobby Roberts, who's my chief scout at Derby: `I daren't tell the lads how bad Leatherhead are - they may get complacent.' We lost 1-0."
Wherever he went - and his hybrid of old-school geniality and progressive ideas about tactics and players took him to Blackburn, Birmingham, Oxford, Queen's Park Rangers and Newcastle - it was the same Cup of woes. Three times he went out in the fifth round, while Newcastle once played four games, as many as it takes some teams to qualify for the semi-finals, yet still lost to Watford in the third round.
The one time he did reach Wembley, with QPR in the 1986 League Cup final, they were thrashed 3-0 by the Oxford side he had built and left. "The whole day was weird for me. We were lined up in the tunnel and I realised I knew their players better than my own."
His FA Cup fortunes seemed set to change at Portsmouth, whom he took to Bournemouth before each round (Derby have spent the past two days at bracing Bisham Abbey). In the semi-final, Pompey led Liverpool through Darren Anderton's goal until Ronnie Whelan equalised deep in extra time. The replay was goalless when, in the 87th minute, glory again beckoned Smith.
"John Beresford got to the byline and pulled the ball back. The keeper had gone to his near post, so the goal was gaping, and if we had one player you'd have backed to score it was Alan McLoughlin. But he caught it too hard and hit the bar. Liverpool could hardly lift their legs but that helped them get through the extra half hour."
Portsmouth lost the penalty shoot-out - an outcome Smith felt trivialised the competition - and became the first team ever to go out of the Cup without losing. "I've always regarded myself as a bit unlucky with that one," he says with wistful understatement. When Derby lost to Middlesbrough in the sixth round two years ago, he could have been forgiven for believing the FA Cup gods bore him a grudge.
But maybe, applying the perverse logic of the competition, Smith's luck is about to be turned on its head. For in the League Cup, always kinder to him, Arsenal beat Derby at Pride Park with a shadow XI. "The beauty of the FA Cup," he argues, "is that you don't bring any baggage into a tie."
Smith admires Arsene Wenger's coaching flair (while wondering how the Frenchman, Gianluca Vialli and Ruud Gullit would fare without resources at, say, Halifax or Oxford). He sees Nicolas Anelka and Dennis Bergkamp as "very special talents", and got as far as speaking to Emmanuel Petit on his mobile when he became available at Monaco.
"If we were going to Highbury in the Premiership, we'd probably set out to be pretty defensive and try to hit them on the break. The Cup is like a one-off, with the fallback of a replay, and the mentality is to go for it. Try to win."
Three wins, and Wembley would be truly, madly Derby's. Cliff Richard ended up with a knighthood. Jim Smith will settle for the celebrated silver pot.