For he has twice finished a loser with Preston and suffered a third final heartache from the Millennium Stadium sidelines after being sent off against North End as Leeds United booked their final slot only to lose 3-0 to Watford in 2006.
Cresswell is hardly proving a jinx for the Blades, however, five goals from 12 games already having repaid a chunk of the 250,000 investment manager Kevin Blackwell made in securing his services from Stoke.
"I just thank God the final is not going back to Cardiff – I don't want to go back there again," said Cresswell after his match-winner against Middlesbrough.
"I imagine the play-off final is probably the best game to win but I know it is the worst game to lose and I don't want to lose one again. Once is enough, but three times leaves a wound and, in fact, it wouldn't surprise me that if we do get there they leave me behind!"
The Blades will not be content just to sit in a play-off slot after returning to the top six for the first time since October 3.
"We never say never about getting into the top two. They are on a great run, especially Forest, but everyone takes a dip in form at some time and it is up to us to push them all the way and, hopefully, they might slip up at some point and we can benefit from that," said Cresswell, enjoying his run up front rather than being consigned to the flanks.
The 32-year-old is ideally placed to know what is required to mount a challenge and says: "We won't settle for a play-off place. It is going to be tight. I have been in promotion races before and managed to get there and I know what it takes. This club is known for pushing on after Christmas and if we can do that we can be there or thereabouts.
"It takes a lot of team spirit, you need lads to stick together with everyone working for each other. The secret is trying to keep as many people as fit as possible and have competition for places.
"The gaffer has been on about competition breeding enthusiasm and results and when you saw the bench today it was strong and the 11 on the pitch know they have to perform or they will not start."
It took the said starting 11 a long time to perform to their maximum on Saturday, however – Kyle Walker for right-back Derek Geary being the only change to the side which had won in the FA Cup at QPR in midweek.
The Boro, in fact, shaded a dour first half which took 30 minutes to produce its first shot, Isaiah Osbourne breaking into the area to test Blades goalkeeper Mark Bunn.
Boro are a work in progress under manager Gordon Strachan, only three months into a four-year contract, and they paraded three debutants from the manager's former club Celtic, flank duo Barry Robson and Willo Flood and target man Chris Killen.
They look astute signings, well equipped for the physicality of the Championship with Robson in particular having that edge to his game which is going to upset opponents – though Killen matched his team-mate's aggression with an elbow into the face of Cresswell in the centre circle.
The second half was much better fare thanks to Cresswell's strike. It came in the 55th minute when left-back Andy Taylor played a free-kick out to Ched Evans, took the return and bent in a cross from deep, allowing Cresswell to hurl himself in front of David Wheater to turn the ball past Danny Coyne in front of the Kop.
The game unfurled with Boro having a penalty shout turned down at one end as Jeremie Alladiere went down attempting to get between Marcel Seip and Walker before Cresswell felt hard done by within 60 seconds at the other end following a challenge from Chris Riggott.
An ankle injury to Alladiere diminished Boro's threat and the Blades began to boss proceedings, a first-timer from James Harper going over after Evans set up Quinn for the cross and then knocked it into the path of the onrushing midfield man.
Quinn and Harper again combined through the middle but when the latter went down under Riggott's challenge, the ball broke for substitute striker Henri Camara, whose sidefooted effort beat Coyne but struck a post and rebounded back to the goalkeeper.
Boro's highly-rated substitute Adam Johnson caused problems but Blades captain Chris Morgan had a tremendous game at the heart of the home defence, slightly shading the performance of loaned back Spurs defender Walker, who got a bloodied nose from Robson as a reward for a display which made his area of the pitch a cul-de-sac for the ultimately frustrated visitors.
Sheffield United: Bunn, Walker, Morgan, Seip, Taylor; Williamson (Ward 70), Montgomery, Harper, Quinn; Evans (Camara 70), Cresswell (Henderson 89). Unused substitutes: Bennett, Stewart, Geary, Fortune.
Middlesbrough: Coyne, McMahon, Riggott, Wheater, Hoyte; Robson, O'Neil, Osbourne, Flood (Franks 75); Killen, Alladiere (Johnson 63). Unused substitutes: Bent, Arca, Bennett, Steele, Williams.
Referee: A D'Urso (Essex).
Hero: Chris Morgan
The Blades captain and central defender, right, is on top of his game at present and ensured they kept a fifth successive league clean sheet at home for the first time since 1984 – a key factor in helping them secure 20 points from the last 27 available.
Villain: Barry Robson
This feisty 600,000 signing from Celtic certainly put himself about, earning a yellow card for a challenge on Stephen Quinn, flattening Mark Bunn and bloodying the nose of Kyle Walker and was a threat, too.
55th-minute: Richard Cresswell throws himself in front of David Wheater to convert the cross from Andy Taylor.
Andy D'Urso: Clearly wasn't a 'homer' and five bookings, including a fifth of the season for Quinn, seemed a tad excessive.
Both the Blades and the Boro are going to be mighty difficult teams to beat but the Bramall Lane club look the best equipped to sustain a promotion bid.
Bolton Wanderers v Sheffield United, FA Cup, 4th round, Saturday, 3pm.
Quote of the day
My face was in the mud at the time
the ball went in but
when I heard the cheer I knew I had scored.
– Blades match-winner
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