An injury-time equaliser from Aruna Dindane prevented the Black Cats from claiming a first win in 12 matches at Portsmouth after Darren Bent put the Wearsiders in front from the penalty spot.
Bent's strike followed the dubious spot kick award and dismissal of Pompey defender Ricardo Rocha in the 12th minute, but Sunderland failed to make the most of the extra man.
After Portsmouth boss Avram Grant was sent to the stands for complaining about Friend's decisions, Sunderland midfielder Lee Cattermole was sent-off nine minutes after half-time.
Cattermole did not heed Bruce's warnings at the break, earning two yellow cards in six second half minutes.
To add to Bruce's misery, David Meyler also faces a three-match ban for an elbow on Tal Ben-Haim six minutes from time.
The two of them, for me, are stupid and it's cost us the game in the end, said Bruce.
I can't defend them. Catts has just been booked and while the yellow card is questionable he has to learn that even if it's a disputed ball, it makes the ref's mind up.
With all the carry on that has gone on in the first half we didn't need to give them any advantage.
It was all we spoke about at half-time, don't give the referee a decision to make. In their defence they're both young and honest boys but they will have to learn from that.
It's four games now where we're leading in the last few minutes and we've been pegged back. To say I'm shattered is an understatement.
Grant's decision to remonstrate with Friend on the Fratton Park turf after the halftime whistle might have earned him a seat in the stands after the restart, but it helped to galvanise the Portsmouth players.
And, with Sunderland now heading to Arsenal a week on Saturday five points above the relegation zone, Bruce could not hide his frustration.
They put the referee under an enormous amount of pressure, the crowd and Avram,
he said. There were howls and derision from everywhere but the referee made the right decision.
What all the fuss was about after that I don't know but the one thing we need to be is a bit more professional after that. It threw all the impetus back to them. When we went down to ten men we had all the chances. To get done in the last ten seconds, like we were at the Stadium of Light against Portsmouth, is frustrating.
Portsmouth's late leveller could prove to be their last goal in the Premier League, with the club in the High Court at 10am today hoping to adjourn the appeal against a winding-up order.
They hope to avoid administration or liquidation after the tax authorities claimed to be owed around £7.5m.
Grant said: When you go to court it is a clear case most of the time. It's normally between two people. This is about 250,000 people, these players here. It's not a normal business. I said to the Premier League not to punish the people, the fans, they don't deserve it. It's not an easy decision, but they have to think about more than the money.''