Sunderland started the year with a win and a Josh Maja goal, but it was to be one of his last as a shambolic January began to dismantle the Lads great start.
Maja, who’s contract discussions had stalled, notched the winner in the 23rd minute at Blackpool on New Year’s Day, putting the Lads only two points behind Luton Town, with two games in hand.
Wins over Newcastle U21s and Manchester City U21 had also put Sunderland into the Checkatrade semi-finals, but our league form really started to falter.
With continuous speculation surrounding the future of Maja affecting the club’s performances on the pitch, Ross and Sunderland gradually began to perfect the infamous 1-1 draw, letting a one goal lead slip for three weeks running in games against Luton, Charlton and Scunthorpe.
The month ended with the news nobody wanted to hear, with chairman Stewart Donald admitting Maja had refused to sign his contract, and swiftly allowing him to move to French side Bordeaux for an undisclosed fee.
A last minute deadline day scramble to replace Maja meant Sunderland splashed out a League One record £3m deal for Wigan striker Will Grigg... although nobody was too sure what they hell William was wearing on his feet (see photo below).
Grant Leadbitter would also rejoin the club, as he made an emotional return signing on a free transfer following weeks of speculation.
It was player of the season Aiden McGeady who would take the headlines though, as his superb solo effort gave the Lads a 1-0 win over basement club AFC Wimbledon.
Grigg’s fellow January recruits Grant Leadbitter, Lewis Morgan and Kaziah Sterling all made impressive debuts in the victory, though the 1-1 draw would soon return with a vengeance for Ross.
After a quiet debut at Oxford United, Grigg announced his arrival on Wearside by missing an open goal in a, you guessed it, 1-1 draw at home to Blackpool.
Sunderland put in one of their worst performances of the season live on Sky, having to come from two behind against Accrington Stanley, but ended the month with two impressive victories over Gillingham and Bristol Rovers.
Concerns started to creep into the fanbase, as we ended the month in third position, two points behind Barnsley, but with a game in hand.
Whilst most Sunderland fans will remember March being all about the sheer panic of knowing whether they could obtain enough tickets for the Lads’ trip to Wembley, the month did bear witness to the return of Sunderland’s early season positivity.
Lee Cattermole finally revealed himself as the goal-scoring God we always knew he was, with The Lads racking up home wins over Plymouth and Walsall, all whilst gaining a credible point at promotion rivals Barnsley and a memorable Checkatrade semi-final win over Bristol Rovers.
But, despite ending in shoot-out heartbreak, the month would end in a memorable weekend in Trafalgar Square, with Wearside painting the capital red and white as we made sure Wembley shook with the sound of Sunderland joy.
After the breathtakingly fun Checktrade Trophy final weekend, the Lads started the month in mesmerising form - but would unravel in spectacular fashion come month end.
A 3-0 win at Acrrington Stanley was followed by George Honeyman’s last minute winner at Rochdale to put Sunderland level on points with second placed Barnsley, still with two games on hand.
However, in true Sunderland fashion, the Lads proceeded to drop points to Burton Albion (1-1, you guessed it) before a season changing bizarre 5-4 defeat at home to Coventry City took the Lads off course for promotion with only five games of the season remaining.
Fan group the Red and White Army showcased their new magnificent flag display, but a morale boosting Good Friday victory over Doncaster Rovers was quickly wiped out by a crushing draw at Peterborough that effectively sealed Sunderland’s play-off fate.
41,000 fans would witness Sunderland battle to a 1-1 draw with would-be play-off opponents Portsmouth, before a poor 2-1 defeat to the irritable Joey Barton’s Fleetwood meant we could no longer, mathematically, gain automatic promotion.
After only losing three games all season, Sunderland managed to lose two in four days as a late Stephen Humphrys goal rescued Southend from relegation, and condemned Sunderland to a fifth place finish and a two legged play-off tie against Portsmouth.
Despite a poor end to the season and the fact Sunderland had failed to get the better of Pompey all season, Jack Ross’ team put in a terrific second half performance in the first leg, with super sub Chris Maguire blasting home to give Sunderland a one goal advantage.
A week of boxing like ‘trash talk’ from a barrage of Portsmouth players ended up being nothing more than Brett Pitmann shouting at a ball-boy, as Sunderland’s players put in a heroic performance to send the Lads back to Wembley.
Wallets across Wearside winced as Trafalgar Square prepared for another invasion.
Another amazing weekend in London ended in heartbreak though, as Jack Ross and Sunderland’s season ended in the cruellest of fashions.
A bizarre opening goal from Naby Sarr had given Sunderland the lead in only the fourth minute, but with half of the ground still bemused as to what they had just seen, Charlton left-back Ben Pennington dragged the Addicks level in a pulsating League One play-off final.
With the final whistle due to signal extra-time, Lee Bowyer’s side left Wearside shell-shocked with the latest of late winners to send Charlton fans delirious and Sunderland fans into despair.
With many fans sat in complete silence, a stoney faced Jack Ross and his Wearside faithful faced up to another kick in the teeth.
Talk of a “100 point” season was rife on Wearside following Charlie Methven’s ambitious statement on the Roker Rapport post play-off Podcast - and how Charlie would come to regret that quote.
Dylan McGeouch and Reece James confirmed extensions to their Wearside contracts, as the rumour mill linked Jon McLaughlin with a move to Championship side Millwall amid speculation about the Scottish goalkeeper not yet signing a new contract.
Robbin Ruiter, Adam Matthews, Max Stryjek, Luke Molyneux and Connor Shields were released from the club as, unbeknown to anyone, Jack Ross contemplated resigning from the club.
The month started with the sad announcement that cult-hero Lee Cattermole was departing the club after a decade of crunching tackles, battle cries and admiration of the ‘Boro Xavi. As Tom Walsh said in his farewell letter to Lee, “we are all Lee Barry Cattermole”.
Lamine Kone also completed a permanent move to Strasbourg, in return for a Wham bar and a visit to Beamish.
To soften the blow, Jack Ross would bring in his first signing of the season in Conor McLaughlin, which actually seemed like a great idea at the time.
One became two in less than 24 hours, with alleged “dodgy” ‘keeper Lee Burge the second through the Stadium of Light doors, signing on a Bosman free from Coventry City.
Both players would play as Sunderland started their pre-season with a routine 2-0 victory over South Shields thanks to goals from Ethan Robson and Luke O’Nien before jetting off for a pre-season tour of Portgual.
Ross would sign up another former Coventry man, bringing in Jordan Willis on a Bosman free transfer as Sunderland 19/20 side began to take shape.
Sunderland’s opening game in Portugal would see us line-up in an unusual 3-4-2-1 formation, as we played out a 0-0 draw with Benfica’s B team. Hearts broke across Wearside, with the confirmation Donald Love had taken his love to Shrewsbury Town.
Sunderland completed their pre-season tour with a 1-0 defeat to Mika’s Belenenses.
Rumours of a takeover continued to hinder Sunderland in the transfer market, with numerous newspaper outlets confirming New York businessman Mark Campbell was close to a takeover of the club - as we now know though, the takeover would never happen.
Hair gel sales would rocket throughout Wearside as former Arsenal youngster George Dobson completed his long protracted move to the club for an undisclosed fee, and he was joined by Marc McNulty, who joined on loan from Reading.
Sunderland would end their pre-season with a disapointing 1-0 home defeat to Heerenveen, as Bryan Oviedo joined Kobenhavn on a free transfer.
Out of the blue, the month began with the surprising sale of captain George Honeyman, who joined Championship side Hull in a reported £250k deal.
Jack Ross’ side would obliterate any excitement for the new season by continuing where they left off, with two poor 1-1 draws at home to Oxford United and Ipswich Town.
Fans bemoaned the bizarre three at the back formation which appeared to hinder, rather than improve, Jack Ross’ team. Despite wasting an entire pre-season trying to perfect it, Ross ditched it within two games.
A morale boosting 3-1 victory at Accrington Stanley in the league cup would send Ross’ side on a five game winning run, with an impressive win over promotion rivals Portsmouth followed by wins over Rochdale and AFC Wimbledon.
Perhaps most impressively though, a much changed Sunderland team would knock out Premier League side Burnley, as the Lads came from 1-0 down to grab a sublime 3-1 win over Sean Dyche’s side, with goals from Grigg, Dobson and Flanagan.
It would not be Sunderland if things continued to go this smoothly though, would it? Typically, the Lads would end the month with a 3-0 defeat at Peterborough United, with Posh’s star man - and supposed long-term target - Marcus Maddison destroying nine man Sunderland, who had both Luke O’Nien and Charlie Wyke sent off.
Sunderland would make one final signing before month end, bringing in Joel Lynch on a free transfer.
The loan signing of Laurens De Bock would complete Sunderland’s summer, as fans began to fear the worst following defeat at Posh and a poor transfer window.
It all began to unravel for Scottish boss Ross this month, although the fan-base was boosted by huge rumours the a consortium of billions, fronted by Michael Dell, were ready to take over the club.
Despite a 3-1 win, some fans unhappiness with the performance at Accrington Stanley led to a Jack Ross outburst, claiming the negativity was “an anchor holding back the club”. Ross would, of course, follow up that comment with two 1-1 draws, one of them a disastrous last minute rescue at crisis club Bolton Wanderers.
Fans were angry, but at least we could console ourselves that we would soon be very, very rich... right?
Ross did enjoy a slight reprieve with another Premier League scalp, this time over Sheffield United in the League Cup, before the month ended with a 2-1 victory over MK Dons.
October began in the worst possible way.
News had reached fans that Michael Dell’s takeover was apparently off and, rather bizarrely, manager Jack Ross was sacked hours later, on a match-day. Despite many fans calling for Ross to be sacked, the timing appeared little more than deflection tactic after the news of the failed takeover.
A visibly upset James Fowler took temporary charge for the Leasing.com Trophy win over Grimsby Town before he himself departed.
A two week search for a new manager ensued, with Kevin Phillips, Nigel Pearson and Roy Keane touted as the bookies favourites, before the depressing rumour that we were about to appoint Phil Parkinson came true. Urgh.
A toothless 1-0 defeat at Wycombe wasn’t the best of starts for Parky.
With fans bemoaning the uninspiring appointment, his Stadium of Light tenure actually began with the clubs best performance of the season as we demolished Tranmere Rovers 5-0 - although that was to be as good as it got, as his team lost two in his first three with a 1-0 defeat at Shrewsbury Town only days later.
Despite dominating the match, the Lads would exit the League Cup on penalties at Oxford’s Kassam Stadium, as Will Grigg fired his penalty well over the bar in a moment that summed up his time on Wearside.
By season end, November is the month we’ll back on as when things truly fell apart for Sunderland. It started well enough, with a second home win and second clean sheet over relegation threatened Southend United, but it would soon become poisonous.
Phil Parkinson’s side would go on to produce some of the worst results in Sunderland history, as they suffered defeats to a Leicester U21s and League Two Scunthorpe before failing to get a shot on target in an extra time first round FA Cup defeat to Gillingham - the earliest we have exited the competition since the early 1920’s.
A brief moment of good came in a 1-1 draw at home to Coventry, as academy graduate Benji Kimpioka came off the bench to rescue an undeserved point, but Parkinson’s side failed to capitalise on it with fans calling for Parkinson to be “sacked in the morning” when they lost at home to Burton Albion only three days later.
Despite calls for his departure, Phil Parkinson remained the manager as we took the long trip to freezing cold Priestfield for our third game in three weeks against Gillingham, although the result would heap further pressure on the manager, as Connor Ogilvie’s last minute winner sent the travelling fans home unhappy.
Sunderland would then play out two unacceptable home to draws to Blackpool and basement club Bolton, with with chants for “Parky out” growing louder. But would Stewart Donald listen? Absolutely not.
The year was rounded off with a win, away at Doncaster, reminding supporters that football can occasionally be fun.