Danny Webb stated Leyton Orient’s 5-0 loss to Accrington Stanley was ‘very hurtful’.
The O’s now sit at the foot of the League Two table with Newport County gaining back-to-back wins.
Sean McConville (2), Matty Pearson (2) and one from Billy Kee were enough for the Orient boss to receive his heaviest defeat since he took over from Andy Edwards in January.
Doncaster Rovers are the visitors to Brisbane Road on Saturday (3pm kick-off) before the club are due in High Court the following Monday.
This is due to the winding-up petition they were given by HMRC over an unpaid tax bill believed to be around £125,000-£250,000.
Webb said: “It was a very hurtful night at the office so to speak, certainly my lowest night in football.
“I have not been in it long in regards to the management side of it.
“But even at Stevenage and against Grimsby I have not felt like this yet.
“It is hard, I am trying to take on a lot. I am sort of carrying a lot of things on my shoulders.
“I am trying to reassure players about winding-up petitions, and I have to reassure myself really because I don’t have a clue what is going on either.
“The whole thing is testing. All we should be worried about is setting the team up to try and win a football game.
“We knew it would be tough against Accrington, every game from now until the end of the season is going to be tough.
“When it went to 2-0 straight after half-time, you are looking at the game and it is said to say it but you think when is the final whistle coming, especially at three, four and five because unfortunately if the game goes on longer you could lose six or seven, you just have to say that’s football.
“That was football in the cruellest horrible way.”
The bad news kept coming in the 33-year-olds way as Nicky Hunt had to come off with an injury and soon after Stanley managed to break the deadlock.
When asked whether that was the reason the home side scored Webb said: “It was not his man that scored the goal.
“He was hobbling that bad if he stays on for the corner and his man gets a jump on him and scores the header you think I wish I had done that substitution was earlier.
“Those two were not connected at all, it had to be done there and then.
“Obviously it upsets the rhythm and sort of having one of your main experienced players going off with an injury was a big blow at that time.”
It was the same old story for the east London club as they conceded only six minutes into the second half when Pearson found the back of the net through a header.
Webb introduced Nigel Atangana at the break to replace Freddy Moncur but insisted the young midfielder did not wrong.
“I know these lads and sometimes you think it wasn’t going to be one of those nights for him,” said the former Southend player.
“Nigel gives a bit more physicality in there and I think he has come on and did quite well.
“I have not seen the goals but the fact they are sort of two free-ish headers is the story of the season, regardless of personnel, ages, young players, older players, that has been the story of the season.
“I think your heart sinks when it goes to 2-0 because you think it is game over when you are down the bottom.
“When you are at the top you can come back and make it 2-2 but down the bottom, it is a big ask.”
One slight positive for Saturday is Liam Kelly will be back following his six-match suspension for shoving a Plymouth Argyle ball boy in the O’s 3-2 victory on Valentines Day.
He said: “It is fantastic to have him back. I think when you go back to that Plymouth game it should have been a springboard.
“But Hunty got suspended, Kels got suspended and it just knocks you back.
“I suppose in a weird way you are due a night like this down the bottom.
“I don’t think the Stevenage score was harsh. And me being the ever optimist I did see things in individuals which only I would know as I seem them in training, individual progressions. But that is hard to stomach when the result is that bad.”
Charlie Grainger has now conceded eight goals in three games since taking over from Sam Sargeant following the 4-1 loss to The Boro.
The O’s boss was asked whether senior keeper Alex Cisak would be back in contention for Saturday and he admitted: “Yes. He is in contention for every game. I think it is very harsh as we have to be careful as fans and people not to start pointing the finger. I think the last goal has come off Charlie’s head and if you see him in there he is low. We have three strong goalies, I will decide on Thursday, Friday who we play in goal on Saturday.”
Webb also said he wasn’t in contact with owner Francesco Becchetti.