SAINTS lost a must-win game to promotion rivals in the 97th minute and that still finds itself tied for most deflating moment of the day.
The enthralling contest at Ipswich Town, resulting in a 3-2 defeat, was made even more frenetic by off-the-pitch matters.
News of Manchester United's official approach for Saints director of football Jason Wilcox broke in the minutes building up to the clash.
The story developed throughout the evening leaving many supporters scratching their heads in search of answers.
Here is everything we know about Wilcox and Man United...
What do we know about Man United's approach?
Man United made an official approach to name Saints director of football Wilcox their new technical director.
They offered Saints a compensation fee equivalent to a year's salary for Wilcox for the former Man City boss to begin working immediately.
The Premier League giants believe this a fair offer owing to Wilcox's arrival on the south coast just nine months ago.
Man United insist they have approached fairly and they hope to find an "amicable" solution to the saga.
However, Saints were set to reject the offer - which they do not see as satisfactory, given Wilcox's importance and the timing.
They are prepared to negotiate but insist on Man United paying a higher fee if they are to release Wilcox from his notice period - 12 months.
It was reported during the fixture at Portman Road that Wilcox resigned from his post, although official confirmation of this has not come.
Wilcox was not in attendance at the match, which saw fourth-placed Saints visit the league leaders.
Liverpool were briefly linked with a late move for Wilcox on Monday evening but this is understood to be untrue.
Unless Man United agree to a higher compensation fee, Wilcox will not be able to begin work for the Old Trafford side for his notice period.
Wilcox's former colleague Omar Berrada is set to join Man United from Man City at the end of the season as the club's new CEO.
What has Wilcox done at Saints since arriving?
Wilcox, in an interview with the Daily Echo last summer, confirmed he was a major driver behind the appointment of manager Russell Martin.
“Russell is my hire. I have to get approval from the board but he’s my responsibility. I interviewed lots of high-profile managers," Wilcox told the Daily Echo.
“The reason I came here is because of the vision of the owners, I met Henrik (Kraft) and Rasmus (Ankersen) on numerous occasions.
"Then I met Dragan (Solak), and his passion and his frustration at how things have not gone according to plan.
"My job is to improve us on the pitch, it’s a really exciting time.”
The 53 year old has also overseen the appointments of backroom staff and a new academy setup, including director Andy Goldie.
This includes the appointment of under-21s and under-18s coaches, including former Man City academy coach Calum MacFarlane.
“If I need to make big changes in infrastructure or staffing I will speak to Phil Parsons or Sport Republic," Wilcox told the Daily Echo.
The director of football has orchestrated a possession-based style of play right down the age groups at Staplewood.
Wilcox has also played a big hand in recruitment. Saints spent £12million on Man City under-21s captain Shea Charles in the summer.
Saints spent £10million on Sunderland striker Ross Stewart, who has barely kicked a ball this season through injury.
However, they have had much greater success with astute loans including Flynn Downes, Man City's Taylor Harwood-Bellis, and Ryan Fraser.
What has Russell Martin said about the news?
The Daily Echo asked a frustrated Russell Martin about the reports following the match and the boss delivered the expected response.
He said: "If you give me at least 10 minutes to get over the disappointment of tonight, then we will chat sometime this week and I'll have more for you.
"I have not spoken to the club. You know my feelings on Jason and I will have a chat with him after.
"I have just had a text saying how proud he was of the performance. Once I am told more I'll tell you.
"I don't know if he was here. He doesn't travel with the team so I don't know whether he was here."
Speaking to Sky Sports, Martin said: "I have been hearing for six weeks in the media that he is going to leave.
"Nothing has changed. We spoke this morning. We just had a game so I am here to talk about the game and not Jason.
"I am sure, at some point, that the club will be able to tell you or I will be able to you. Right now, I just want to talk about the game.
"I am here to talk about the game. Jason has been great for us. If he leaves, he leaves. But let me be annoyed about this result for a bit first."
What do we think will happen?
The most likely outcome seems that news of Wilcox's resignation will eventually be confirmed.
A future at St Mary's is unlikely and Wilcox could be put on gardening leave throughout his 12-month notice.
Saints will stick to their position on receiving compensation in excess of a year's worth of salary for Wilcox from Man United.
It would mean Wilcox faces a lengthy wait to begin work at Old Trafford, unless Man United stump up the cash.
In February this year, Newcastle United announced that sporting director Dan Ashworth had been placed on gardening leave.
The former Brighton recruitment ace had told the Magpies that he wanted to join Man United and new minority owners INEOS.
Man United were said to be unwilling to pay a fee up to £20million requested by Newcastle as compensation for the 53 year old.
A new director of football would need to be appointed by Saints and Sport Republic chiefs Henrik Kraft and Rasmus Ankersen.
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