4 matches I'd change the results if I could:

Chelsea FA cup
Leeds away 97
Villa away 89

Probably in that order
Cup games before league games, yes. I don't honestly think surviving in either of those seasons would have set us up to establish ourselves as a top club. They might have given us a chance to win a cup of two though, and a cup win is forever.
The one for me was Schwarzer getting injured in the 3 points season. Had that not happened I'm pretty sure we would've got enough points to have stayed up and might not have conceded so early in the FA Cup final.
Nigel Pearson was out injured also at a critical point that season. Had he not been then I think we would have escaped relegation
I think every possible regret that I can think of has been mentioned already. I agree with them all, although can't remember the Norman Bell one. What was that?
Birmingham in FAcup 75.After beating them in league twice 3 0 Jack's tactic was not to go over the half-way line
You could say had we stopped up in 88/89 our history could have shaped up to be alot different

Had pears not got injured or we'd signed someone other than Peter Davenport we could have been north east topdogs for a few years until Newcastle's revival

The firesale of Downing, Alves, Huth, Tuncay and later Adam Johnson would we have bounced straight back

Replacing Southgate with Strachan that set the club back many years

Leaving Ayresome Park but like Sunderland the time was right
Good shout on the Southgate one - I totally agree. Many people slag Southgate off for his time here as manager and say it was a mistake to appoint him. Well if it was then it was an even bigger one to sack him and replace him with Strachan. That was the worst decision Gibson ever made in regard to managerial appointments.
On a personal level, not going to a European away game. Right now European football feels like a VERY long way away so that’s a huge regret TBH.

Generally, the Heskey equaliser at Wembley sticks out. I genuinely think if we’d won that cup we’d have stayed up and given Chelsea a much better game in the FA Cup final.
On last Match at Ayresome Park Day the late great Brian Clough said to the late great George Hardwick "Do you know George, I should never have left this Club" what if somehow we had been able to keep him here ? the mind boggles.
This one hasn’t been mentioned but I remember feeling absolutely gutted afterwards and so deflated…

In the 2014/15 play-off season the last minute goal in the game against Fulham when Dimi came forward for a corner and we ended up losing. Bournemouth played on the Monday night and won, meaning they had a 3 point gap between us and them, with a massively superior goal difference.

A point would’ve meant that even if Bournemouth won, we could still overtake them on the final day if results went our way.
I think every possible regret that I can think of has been mentioned already. I agree with them all, although can't remember the Norman Bell one. What was that?
That game was televised, because I had it taped. It must have been wiped by both ATV and Tyne Tees because I've never seen a clip of it anywhere.
The 2004 transfer window. The team had just won the League Cup and now the town was buzzing over the signing off Hasselbaink and Viduka. Up to that point Juninho was great but playing in the hole behind these two, especially after linking up with Hasselbaink at Athletic Madrid when he scored 24 goals that season, was mouthwatering. Then McClaren buys Ray Parlour to replace Juninho and Juninho ends up at Celtic! What a waste! (n)