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We start our journey way back in 1923 when the club was involved in the first FA Cup Final at Wembley Stadium against West Ham United. An estimated 200,000 people turned up in London to witness the final even though the official attendance states that 126,047 where present. A White Police horse called Billy stole the headlines as he was brought in to ease crowd congestion which had spilled onto the pitch meaning that there was a delay in the kick off. Once order had been restored it took David Jack just two minutes to open the scoring for Wanderers, shortly after the second half John Reid Smith doubled the teams advantage when he lashed home a powerful shot past the Hammers goalkeeper Hufton to secure Wanderers their first ever FA Cup Trophy.
Many of the 1923 Final team appeared in the next two FA Cup Finals that the team reached and in and in the 1926 truimph it was David Jack who was once again the hero in a 1-0 win over Manchester City however the heroics of the "Topsham Fisherman" Dick Pym in the Wanderers goal prevented our Manchester neighbours from getting more out of the game.
The 1929 Final and the third FA Cup win for Wanderers in the 1920's was hampered due to the fact that Pym was carrying an injury which lead to an enorm of first half pressure by opponents Portsmouth, however the Wanderers defended stoutly and late goals by Billy Butler and top goalscorer Harold Blackmore made the game safe for Bolton.
Perhaps one of the most remembered finals in Wanderers history is in fact one which ended in defeat. Lancashire rivals Blackpool came back from 3-1 down in the 1953 FA Cup Final to win the game 4-3 thanks to a hattrick from Stan Mortensen and some wizadry by the legendary Stanley Matthews. It is worth pointing out that the Bolton full back Eric Bell sustained an injury early on in the game and due to the fact that there was no substitutes in those days Bolton had to make do with what they had. Willie Moir, Nat Lofthouse and a header from the injured Bell had put Wanderers in front with Mortensen scoring for Blackpool. Mortensen added two more in the second half and an injury time goal from Bill Perry gave the Seasiders victory in what is now known as "The Matthews Final".
Five years after the Blackpool defeat Wanderers where successful on FA Cup Final day this time against arch rivals Manchester United who had sadly lost most of their side in a tragic Air Disaster in Munich just a few months previous to the final. It was fitting that Boltonian Nat Lofthouse would be the man to bring the cup home to his beloved Bolton although the second of his two goals on final day would raise many eyebrows in today's game due to the fact that he bundled United keeper Harry Gregg into the goal to score Wanderers second goal after the Northern Irishman failed to hold a shot by Dennis Stevens. That incident is still talked about when old rivalries are mentioned between the two sides and despite this Lofthouse and Gregg have always remained freinds outside the football arena.
Then 28 years later Wanderers faced a final of a different kind in the Freight Rover Trophy, no longer having a team able to compete for FA Cup Final success they found themselves struggling in the Third Division in the hands of rookie player-manager Phil Neal who himself was one of the most decorated players in terms of honours in the games history. Bristol City where the opponents on what was a day to forget for Wanderers. Two goalkeeping mistakes by the out of favour Simon Farnworth lead to the South West club gaining victory, regular keeper David Felgate, on loan from Grimsby Town was refused permission to play in the final. Two goals from Glyn Riley and one from Howard Pritchard meant that Wanderers hard work came to nothing despite top scorer Tony Caldwell hitting the crossbar in the first half.
On a sunstroaked Wembley turf in 1989 Wanderers recorded their best ever victory in a final, Once again Wanderers where hoping to win the trophy that had eluded them three years previously, this time Devon club Torquay United where what stood between glory in the newly named Sherpa Van Trophy. Dean Edwards gave the Gulls a shock lead but Bolton born Julian Darby was on hand to level the scores. Regular Torquay keeper Kenny Veysey missed the match so it was up to the experienced Kenny Allen to be in goal. Jeff Chandler then increased Wanderers lead shorly after the hour but the ball blatently cannoned past Allen by Torquay defender John Morrison. Dean Crombie then raced from the half way line to score a rare goal whilst Trevor "sumo" Morgan converted Stuart Storer's cross to give Wanderers their first win at Wembley since 1958.
The Play Off run of 1991 saw two exciting semi final legs against local rivals Bury in which a goal by Tony Philliskirk sent Wanderers to Wembley to face another North West side in the shape of Tranmere Rovers. The Merseysiders seemed more prepared than their Lancashire neighbours and in extra time they secured promotion thanks to a goal by Chris Malkin which appeared to be offside but despite this the Birkenhead club gained promotion to Division 2 despite Wanderers finishing with more points in the league.
1995 saw a double Wembley appearance in finals for the Wanderers. Firstly they took on Liverpool in their first ever League Cup Final. Two goals from winger Steve McManaman gave the Reds another trophy to add to their impressive cabinet, McManaman had tormented the Bolton full back Scott Green all afternoon and was able to pick his spot for both of the goals. Alan Thompson replied for Bolton with a stunning shot on the turn following a cross by debutant Gudni Bergsson but for Bruce Rioch's men it was so near yet so far.
However just over a month later they made one of the most impressive comebacks in play off final history. 2-0 down to Reading within half an hour due to goals from Lee Nogan and Adrian Williams it looked all over when the Royals where awared a penalty but Stuart Lovell saw his spot kick well saved by Bolton keeper Keith Branagan. Owen Coyle pulled a goal back for Wanderers in the 75th minute with a header and the then record signing Fabian De Freitas sent the game into extra time when he raced clear following a pass from the impressive Jason McAteer. McAteer then set up Finnish international Mixu Paatelainen with a header before De Freitas added a second with a close range finish after his first attempt had hit the post. Reading player-manager Jimmy Quinn pulled a goal back with a few seconds remaining but this final ensured Wanderers played in the Premiership for the first time.
Following relegation at the end of the 1997-1998 season Wanderers aimed to book their place back into the Premiership at the first attempt in the 1999 Play Off Final. In their way stood Watford who themselves where looking for a return to the top division having had a succesful period there in the early 1980's. On the day Wanderers where just simply not good enough, despite an early chance by Eidur Gudjohnsen it was the Hornets who took control of the game and they opened the scoring thanks to a spectacular over head kick from Nick Wright despite the best efforts of Bolton defender Neil Cox to head the ball off the line. Wanderers tried hard to find an equaliser but it wasnt forthcoming and with seconds remaining Allan Smart raced clear to fire home the Watford winner after substitute Scott Sellars had given the ball away in what was his final Bolton appearance.
The 2001 Play Off Final, and a first visit for Wanderers to the impressive Millennium Stadium ended in success with a mouthwatering 3-0 win over local rivals Preston North End to return to the Premiership. On the quarter hour mark Gareth Farrelly hit his third goal against the Lillywhites with a fine 20-yard drive. Goalkeeper Matt Clarke, on loan from Bradford City had to be alert to keep out North End duo David Healy and Jon Macken and in the final two minutes both top scorer Michael Ricketts and Jamaican international Ricardo Gardner ensured Bolton gained back their Premiership status.