Blessingindisguise first saw a racecourse as a two year old in April 1995 at Pontefract. Despite finishing unplaced, he lost his maiden tag at Newcastle next time out, taking the Big Dipper Maiden Auction Stakes (Class F) with a three length beating of Silent Soprano.  He was placed twice before tackling the Windsor Castle Stakes at Ascot in June under Derby winning jockey Willie Carson.  He finished tenth, and did not see a racecourse again until April 1996.

Winless through 1996, he was kept busy through the early part of 1997 before scoring at Redcar in May (Dormanstown Sprint Handicap) beating Moon Strike.  He was back in the winners' enclosure at Ripon in June, where he finished half a length in front of Mousehole under Gyles Parkin to take the Racing Channel Handicap.  Blessingindisguise ran a great race next time out, and was narrowly beaten in a thrilling finish by old pal Moon Strike in the Gosforth Park Cup in June.  However, he made amends a week later, dropped three classes at Haydock, to take the Ellesmere Handicap - a very well backed 11/10 favourite.

It was a close call, though, because the tough five-year-old got up only in the final stride under Terry Lucas to beat Polly Golightly by a short head.

Blessing's next win came in the City Index Rated Handicap (5f), Ascot in July. Blessing landed the race for the second consecutive year, proving he is is a real 5f specialist and had struck form in no uncertain terms in the last fortnight. He was always going well, and it was just a question of whether or not an opening would present itself. A narrow gap did materialise in the nick of time, and he quickened up impressively to win a shade cheekily under big race jockey Michael Kinane.

Blessingindisguise, York 2000

However, Alan Black's star horse was disappointing for the rest of the 1998 season, failing to get his head in front. He returned for the 1999 season at Doncaster, but finished down the field.

During the early part of his 1999 campaign Blessing was unsuccessful, struggling under the huge weight he was allotted after his wins last season.  In an attempt to solve Blessing's dislike of the starting stalls, Mick Easterby designed a guide rein to keep his head up to try and stop his escape attempts. The strap was designed to keep Blessing's head up and help him settle, and it certainly seemed to work.

However, he could still not get his head in front despite being constantly tipped up in the racing press and daily newspapers as his handicap mark slipped further and further.

Blessingindisguise, Thirsk 2000

Blessing was a big attraction at Mick's at the 1999 Malton Open Day, and enjoyed the attention and the polo mints he was given to crunch on by the visitors. He looked superb, his coat glossy and shining and greeted the public in his usual gentlemanly manner.

A fortnight after Malton, Blessing headed for Newcastle and the five furlong Easy Favourites Magic Eleven Fifty Two Handicap. Here he met the in form Brecongill Lad from the David Nicholls stable, and Blessing was sent off as a 10/1 shot. This time Blessing made no mistakes and made just about all under Gyles Parkin to hold Henry Hall by a head and leave owner Alan Black singing the praises of a horse who seemed to have lost his sparkle.

Black said: "He's tried our patience, but we never lost faith and let's hope he can win a couple more yet.

Blessingindisguise, York 2000

Blessingindisguise signed off his 1999 season at Catterick, where he tried to follow up his Newcastle win. However, the track did not suit and Blessing appeared to be over the top after a hard season. He finished fifth to Cartmel Park and headed for his well deserved winter break.

Blessing spent his holiday quite content with himself in a warm barn with three companions at Sheriff Hutton.  He was back in light work in March and returned for the 2000 season at Newcastle.  He ran a good race to finish 5th, apparently running out of steam at the distance.  A week later, and better for the race, he headed for Thirsk and a Class C handicap over 5 furlongs.   After swerving right at the start, he was badly bumped a furlong out and finished eleventh. 

By the beginning of May, the ground had dried out and Blessing returned to Thirsk on 6th May.  This time on his favoured faster ground Blessing ran a great race, finishing second to shock winner stablemate Sulu (a 25/1 shot!), conceding a lot of weight. 

Blessingindisguise at York 1999

Later in the month, Blessing ran at the York May meeting, tackling a five furlong sprint handicap on the Dante Stakes card.   Unfortunately Terry Lucas couldn't do the weight, as he had only 7st 11lb in the race.  Blessing didn't get away from the stalls quickly as he did at Thirsk, and in driving rain and a terrible wind he finished eighth. 

At the York June meeting, everything looked right for Blessingindisguise as he lined up for the Anthony Fawcett Stakes.  He was well drawn in three, where he would get a lead off Westcourt Magic.  The ground was riding fast, and Giles Parkin was back in the saddle.  However, trouble at the start loomed - firstly Swynford Dream was unruly in the stalls and Bodfari Komaite decided to repeat his Doncaster antics by escaping from the stalls.  After the reload poor Blessing wasn't given any time at all to make up his mind and the runners went without him.

Blessingindisguise on Mick Easterby's gallops, 2002, ridden by Terry Wade

After a stalls test, which he passed with flying colours, Blessing tackled the Gosforth Park Sprint Cup, and ran a great race to finish sixth.  Back at the Knavesmire the stalls were this time no problem, as he tried to win the race he took 2 years ago, the Mr Kipling Exceedingly Good Stakes.  He was well backed on the day and ran a blinder.  Leading the field to a furlong out, only Eastern Trumpeter (rec 3lb) could catch him.

Returning to the scene of his last victory in July, Blessing was a very warm order in the Bet With UKBetting.com Handicap at Newcastle. Well fancied and backed, he ran an unusually poor race to finish last of eight to Brecongill Lad. 

Blessing was again on show at the annual Malton Open Day in September, attracting a band of admirers and endearing himself by resting his head on the visitors' shoulders.  Clearly after Polos!!

Blessingindisguise at Beverley, 2001 sporting uncharacteristic black visor and noseband

Blessingindisguise remained unable to get his head in front in 2000, despite two second placed runs.  His last run of the season in soft ground at York was very promising, as jockey Gyles Parkin thought he felt better than ever.  he blazed along at the front until two out, then the sticky ground got the better of him and he finished fifteenth of 23 runners.  The ground certainly didn't help his season as the wet summer and soft ground were anything but ideal for the old fellow.