McClaren steered the side to League Cup glory in 2004 and a runners-up spot in the Uefa Cup final two years later in his five year-spell at the club.
But with his old team currently stuttering in 10th spot in the Championship with one win and a draw in their last 11 games, hope of returning to the top-flight any time soon seems bleak.
"Many clubs are in a similar situation," said the ex-England boss. "They were playing in the Premier League and it wasn't long ago they were in Europe.
"My last game managing them was the Uefa Cup final [They lost 4-0 to Sevilla]. Things since then haven't worked out. It's such a shame and pity.
"I have a lot of respect for manager Tony Mowbray. He's done a terrific job. In the first half the season they were top of the league but something is clearly going wrong.
"It can be anything - injuries, loss of form, not scoring goals. But the pressure and expectation really mounts when you've been a great club and you're falling down to mid-table. The pressure from the media and fans is enormous."
The added weight of expectation is something McClaren, currently out of work, endured during his second spell at FC Twente.
He had guided them to a stunning Dutch title in 2010 in his first stint, but his return 18 months later was not so successful.
"When I went back in 2012, they were third and there was a big difference," McClaren added. "Six players had left and the expectations from the media and crowd were huge. We had won the championship and everybody was asking 'Why can't we win again?'
"Twente were a selling a club. They were such a new team and I just couldn't believe it. The team had disintegrated. We had to rebuild but the pressure was growing. I felt we were over-achieving though and punching above our weight.
"We were joint-top with PSV Eindhoven at the winter break. We were delighted and then the board decided to sell our star player midfielder Leroy Fer to Everton and we got heavily criticised by the media and fans.
"I was upset as well. We started the second half with four draws and a defeat. Everyone was grumbling and our bus was surrounded by angry fans after the next game demanding the heads of players and coaches.
"There were then banners calling for my sacking. The pressure was building and I asked the board if they wanted me to go and they said yes. But that expectation and pressure is something that's coming into the game more and more."