He was the first Leicester City captain to lift a trophy at Wembley and was the Club’s Player of the Season on two occasions. As a manager, meanwhile, he led his first four clubs to promotion from League 1 to the Championship.
Simon began his footballing career at Leeds United, the team he supported as a youngster, and he started by saying: "I went to Leeds when I was 14. I became an apprentice when I was 16 and made my debut against Huddersfield when I was 17, on a Tuesday night.
"Three days earlier I had been in the youth team. Playing in the first team was a big thrill for me and my family. After that I was in first team squads but I only had a few opportunities because they didn’t have many subs in those days."
In March 1992, Simon signed for Little’s Leicester, who were pushing for promotion and a place in the Premier League.
He added: "Just before the transfer deadline day, on a Tuesday night at QPR, I was one of the Leeds subs. The other sub that night was more famous than me. His name was Eric Cantona!
Steve Thomson scored one of the goals when the ball ricocheted to him and he put it away. He still says I had no input in the goal he scored, but I beg to differ!Simon Grayson
"The next morning I got a call telling l me that everything had been agreed for me to move to Leicester. I was sad to leave Leeds but I knew I had to further my career so I drove down to meet Brian, signed and stayed at Leicester for the next six years."
Simon went straight into the first team and played in every match for the rest of the season.
"It was amazing really," he continued. "I went from playing reserve team football at Leeds to playing for Leicester at Wembley in a Play-Off Final a few weeks later in front of 78,000 fans.
“We beat Cambridge United in the Play-Off Semi-Final. It was a tight first leg, a 1-1 away draw, but we won the second game 5-0 at Filbert Street.
"Steve Thomson scored one of the goals when the ball ricocheted to him and he put it away. He still says I had no input in the goal he scored, but I beg to differ!
Grayson was the Club's first trophy-winning captain at Wembley.
"The final at Wembley against Blackburn was on a red hot day. I spent most of the afternoon chasing Gordon Cowans, who was a fantastic player. I can’t remember a great deal about the game. I was young and didn’t really take it all in.
"I just remember seeing my parents after the game and being absolutely shattered. We were devastated that we had lost the Final at Wembley.
"But, based on where the Club had been the previous year, [when Leicester City had narrowly avoided relegation to the third tier], it had been a massive improvement.
"We got the Play-Off Final the following year too, against Swindon Town, but I’d had a few injuries that season. I was sub for the semi-final [against Portsmouth] but I wasn’t in the matchday 14 for Wembley.
"It was unbelievable how the scoring went [pulling back from 3-0 down to make it 3-3 before losing to a late penalty]. I remember the devastation of losing again at Wembley, for the lads playing and for the club in general."
The following season [1993/94], City were Play-Off finalists again and Simon became the first captain in Leicester City’s history to lift a trophy at Wembley, following a 2-1 victory over Derby County.
For the winner, I just remember crossing for Ormondroyd to head it. He should have scored, but Walshy picked up the pieces to score before wheeling away in delight.Simon Grayson
"I was made captain because Walshy [Steve Walsh] had been sent off at Brighton and they took the captaincy off him, Gary Mills was injured and Steve Agnew was not in starting XI, so I was fortunate that Brian gave me the armband.
"It was a fantastic occasion. Derby were favourites to win because they had spent so much money on players like Tommy Johnson and Craig Shaw.
"I was probably lucky to stay on the pitch because I brought Tommy Johnson down when he was through on goal but I escaped with a yellow card. They were in front and then Walshy equalised.
"For the winner, I just remember crossing for Ormondroyd to head it. He should have scored, but Walshy picked up the pieces to score before wheeling away in delight.
"I was on cloud nine walking up those famous steps for the trophy. My only regret was that someone stuck a stupid beanie hat on my head, which was in all the photographs! Winning the Player of the Year Award that year was a nice accolade too."
The following season, Little left for Aston Villa in November 1994. He was replaced by McGhee who could not save the Club from relegation at the end of the season.
Simon recalled: "We found the Premier League really tough. We were playing against the best players and if we made mistakes, or if we didn’t take our chances, we got punished. Brian leaving us was a big disappointment.
Mark [appointed in December 1994] came with his own ideas, a different style of football and some good players, but his stay was brief. We were relegated and then he left half way through the next season when we were near the top of the table.Simon Grayson
"He’d played a big part in laying the foundations for the success that followed. He brought a feel-good factor to the players, to the Football Club and to the city in general. Looking back, though, you can see why he left. He was an icon at Aston Villa who were a bigger club.
"Mark [appointed in December 1994] came with his own ideas, a different style of football and some good players, but his stay was brief. We were relegated and then he left half way through the next season when we were near the top of the table."
Simon played in virtually every game in that 1995/96 season, which saw the appointment of O’Neill half-way through it and which once again ended in promotion to the Premier League.
Thinking back, Simon remembered: "At the start of that season I was told that Mark was looking to sell me, but I didn’t want to leave. I wanted to fight for my place and I ended up playing nearly every game that year."
McGhee left the Club in December 1995. He was replaced by O’Neill, but the new manager only won three of his first 16 games, with the Foxes slipping from third in the table to ninth with only eight games to go.
Simon reflected: "In today’s football, Martin might have found it difficult to survive with those results. After a home defeat against Sheffield United, we were discussing what we needed to do to turn the results round.
"Then Martin went out to speak to the supporters who were protesting. He confronted them and I think they respected him more because he had an opinion and was prepared to have a chat with them."
Neil Lennon and Simon Grayson
After a terrible run of form, City recovered to reach the Play-Off Final.
The season was rescued just in time. New signings Neil Lennon, Muzzy Izzet, Julian Watts and Steve Claridge, as well as the emergence of Emile Heskey, helped to bring about a remarkable upturn in results with the team winning six of the last eight games.
Leicester City scraped into the Play-Off positions in fifth place. Their semi-final opponents were Stoke City.
"In the first leg at Filbert Street, we were under a lot of pressure," Simon recalled. "Kevin Poole made some fantastic saves and the game ended up 0-0. In the second leg, Garry Parker scored the only goal.
"He didn’t score many and that must have been one of his most memorable. The final at Wembley was against Crystal Palace. Both sides played strong and powerful football. We went into the last minutes of extra time expecting a penalty shoot-out.
"Then Martin took Kevin Poole off replacing him with 6'7' tall Zeljko 'Spider' Kalac, who he felt would fill the goal better in a penalty shoot-out. Then, in the final seconds, Claridge shinned a shot into the top corner and penalties weren’t required.
"When he scored, everything seemed to freeze. We knew that there was no coming back for them because it was so late in the game."
Grayson and his team-mates settled quickly in the Premier League.
The following season [1996/1997] exceeded all expectations. Simon added: "Martin built a good team, with great team spirit. We socialised together. We finished ninth, won the League Cup and qualified for Europe. We beat Manchester United in the cup run as well.
"The semi-final was against Wimbledon, who were probably favourites to win. They had good players like Vinny Jones and Marcus Gayle. The first leg at Filbert Street was 0-0.
"At their ground they went ahead and we knew we would have to dig deep but we also knew we only needed one goal because away goals counted double. I was playing left back that day. I remember Parks [Garry Parker] taking a deep free kick.
"I normally stayed back but I went on a run and the ball found its way to me at the far post. I headed it over Neil Sullivan and into the top corner. I’d say that was the most important goal I ever scored.
"The final at Wembley was against Bryan Robson’s Middlesbrough. Every time we went into big games, we were never favourites. They had Emerson, Juninho and Fabrizio Ravanelli. [Future Leicester City manager] Nigel Pearson was their captain.
"Shortly before the final, Middlesbrough had beaten us at home. In that game they 3-0 up at half-time because Juninho had run rings round us. Martin got me to man-mark him in the second half time.
Coca-Cola Cup winners in 1997
City's first season in the top flight included a wonderful League Cup success.
"In the build up to the final all the talk was about man-marking Juninho again and I was thinking, ‘please don’t let it be me. Wembley is an absolute monster of a pitch and I’m not keen on doing that’. Pontus [Kåmark] got the job and took Juninho out of the game.
"It was tactical genius from Martin. The sacrifice Pontus made for the team was absolutely fantastic. Full credit to him for being able to carry out the job Martin wanted him to do on one of the best players in the Premier League.
"At Wembley, I went up for a header early on and twisted my ankle but I got it taped up and got through the whole game.
"Ravanelli put them 1-0 up in extra time, but we dug in and Emile got a late equaliser, which allowed us to get through to the replay at Hillsborough and to win it there, when Claridge scored the winner after extra time."
It was a real tough decision because I’d been at Leicester for six years and had a good relationship with the supporters.Simon Grayson
At the end of the season, Simon was once again Player of the Year.
He said: "It was good to be able to play in nearly all the games and be consistent. It’s always nice to be recognised in what was a successful season playing with really good players."
However, that close season, Simon transferred to Little’s Aston Villa: “I was out of contract that summer. Martin and I had agreed to wait until the end of the season to sort out a new contract.
"We had a good group, and I was happy at Leicester but when Villa, a top four team at the time, came for me it was too good an opportunity to turn down. It was a real tough decision because I’d been at Leicester for six years and had a good relationship with the supporters."
Simon’s time at City was over, but his successful football career continued. In his two years at Aston Villa, he reached the UEFA Cup Quarter-Finals and was playing for a top Premier League side.
Grayson has returned to Leicester as a manager on several occasions.
He moved to Blackburn Rovers in 1999 before going to Blackpool in 2002, where he started to do his coaching badges before embarking on a managerial career.
The first four clubs Simon managed were Blackpool, Leeds United, Huddersfield Town and Preston North End and he achieved the remarkable feat of getting them all four of them promoted from League 1 to the Championship.
Simon has subsequently managed Sunderland and Bradford City, but last summer decided not to renew an option at Bradford City in order to take some time out after 32 years in the game.
Simon concluded by mentioning that he comes from a very sporting family.
His father played cricket and football to a high non-league standard, his brother Paul played cricket for Yorkshire and Essex and this month, his son Joe made his debut for Blackburn Rovers, the first time a father and son had played for that club since the 1920s.
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