Top Six - Bolton Wanderers Heartbreakers

  • August 25, 2015 | By Sean McNeilly
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After Bolton's indifferent start to the season, we look at the 'Top Six' most heartbreaking moments of recent life following the Wanderers.

The start of the 2015/16 Sky Bet Championship campaign has not been ideal for Neil Lennon's side - one goal, two points and a place in the relegation zone. It seems a difficult season may be ahead.

We are fans that have been used to heartbreaking times like this over the years and, here, we take a look at the top six most heartbreaking moments of the 21st century so far.

6 - Holdsworth Misses a Sitter

The 2000 FA Cup final was the last to be played at the old Wembley Stadium and, because of this, the semi-finals were held at the iconic stadium.

Bolton, then of Division One, made their way to the Twin Towers with the help of some handy draws; facing Cardiff City, Grimsby Town, Cambridge United and Charlton Athletic, before Aston Villa in the semi. Hopes were high that Wanderers' second semi-final of the season would fair better than the thrashing Tranmere Rovers handed out in the League Cup earlier in the season.

A neutral might say the game itself didn't live up to much, but it was dramatic to say the least. Earlier in the game, Dean Holdsworth had hit the post and as we moved into the second period of extra time, Holdsworth had the chance to send Bolton to their first FA Cup final since 1958. After Eidur Gudjohnsen had rounded goalkeeper David James, he teed up an unmarked Holdsworth, who somehow succeeded in skying the ball over an unguarded goal from eight yards. Bolton went on to lose on penalties.

5 - 2004 Carling Cup Final

We start with, prior to the day itself, what was a quite superb journey. A cup run that included a win over Liverpool at Anfield and Aston Villa at the Reebok Stadium were just two highlights of, not only that season, but my tenure as a Wanderers fan.

Cardiff was the venue and the day promised much, but only two minutes in Middlesbrough's Joseph-Desire Job made Wanderers' job a lot harder. Another five minutes on the clock and it was 2-0, and too much of a mountain to climb. Kevin Davies did get a goal back, but the Whites were to end the day on the losing side.

4 - Dougie Just Misses Out

After relegation in 2012, Bolton's return to the Championship began with a stutter. This led to Owen Coyle being sacked and Dougie Freedman chosen as the man to replace him. Too many draws followed, before the New Year brought around a change in form.

Eight wins from 10 games left Bolton on the edge of the play-offs and a possible return to the Premier League at the first time of asking. It all came down to the final day. Bolton would face Blackpool, who had only confirmed their safety the week before. A win for the Trotters would guarantee their place in the top six.

However, two first-half goals from the Seasiders was not in the script. Hope seemed over, but Bolton, to their credit, rallied before the half-time whistle was blown and two stoppage-time goals levelled proceedings. The Whites pushed for the winner, but, little did they know at the time, they were in the play-offs as two rivals, Nottingham Forest and Leicester City, were drawing. The full-time whistle went at the Reebok and the scores were still level at the City Ground - we were play-off bound. But Anthony Knockaert scored in the 92nd minute to send the Foxes into the lottery of the play-offs and Bolton haven't been close since.

3 - Big Sam's Era Comes to an End

Sam Allardyce oversaw some of the best times in Bolton Wanderers' history. Promotion to the Premier League was followed by a prolonged stay in the top-flight. Players like Fernando Hierro, Youri Djorkaeff and Jay-Jay Okocha lit up, not only the Reebok, but the country, and European football was played thanks to a 6th-placed finish.

The times were great, stability was there and nothing could touch us. Then the England job became available in 2006 and 'Big Sam' was touted as a replacement for the outgoing Sven-Goran Eriksson. He would eventually be overlooked and Steve McClaren was given the job. Maybe a coincidence, maybe not, but Allardyce would not complete the next season at the Reebok.

Speculation rose early in 2007 that the end was near, and confirmed at the end of April. Allardyce was gone. What has followed has been few highs and many lows, as no one has yet managed to fill the big gap.

2 - Stoke's Big Day Out

Another tale of FA Cup semi-final woe is the penultimate entry of our list. Again, it starts with great joy in the build up - rivals Wigan Athletic were beaten in a replay at the DW Stadium, before away wins at Premier League rivals Fulham and Birmingham City paved the path for Wembley.

A gloriously sunny day greeted fans and players and, especially after such a good away day at Birmingham, confidence was in the air. That confidence, however, wasn't to last.

Stoke came out of the blocks meaning business and were 3-0 up at half-time. Ex-Trotter Jonathan Walters then added two in the second half to pile on the misery. I'll never forget the person in front me speaking as Walters was about to net Stoke's 4th; 'anyone but Walters, please God'. This summed up the day and was possibly a catalyst for the number one on this list.

1 - Premier League Relegation

It's a horrible word isn't it; relegation. 'Bolton are relegated'. There's no reply to that - those three words have so much pain behind them that it's still being felt to this day.

It all finally unravelled at the Britannia Stadium as Stoke, and Jonathan Walters, were again at the heart of a painful day for Wanderers.

Only a win would do and for around 30 minutes of the 90, that's what we were doing. The Davies', Kevin and Mark, had put Bolton in front after initially falling behind. But a soft penalty, converted by Walters, was the final nail in the coffin. A winner couldn't be found so, at the final whistle, Championship football awaited after 11 years in the top flight.

We still find ourselves in the Championship and have probably not been further away from the Premier League in a long time.

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Pos Team Pld Pts
1 Cheltenham Town 40 72
2 Cambridge United 41 71
3 Bolton Wanderers 40 67
4 Tranmere Rovers 40 65
5 Morecambe 40 63
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