10 – Portsmouth 3-0 Plymouth Argyle (1st September 2018)

Argyle have had many battles with Portsmouth over recent years. Indeed, from 2015/16 to 2017/18, the two sides didn’t finish more than one position apart. Games between them, therefore, were often tightly fought, with plenty on the line. Yet, there was a shift in the balance of power this season, and this abject performance at Fratton Park was a clear signal that Pompey had progressed and Argyle had regressed heading into 2018/19.

Derek Adams, serving a touchline ban, made a bizarre team selection. The Scot left Ryan Taylor, Graham Carey and Ruben Lameiras on the bench, opting to line up with five central midfielders playing behind Freddie Ladapo. Unsurprisingly, this meant the forward was isolated, and Portsmouth could dominate the game. They took the lead after 22 minutes when Jamal Lowe squared for Ronan Curtis to slide the ball into the empty net. In the second half, Lowe and Curtis both got on the scoresheet as the hosts ran away with the game.

9 – Oxford 2-0 Plymouth Argyle (13th October 2018)

In the previous league game, Argyle picked up their first win of the season at the 12th attempt with a 1-0 triumph over AFC Wimbledon. It was important for Argyle to get a win on the board, and doubly important because it lifted them off the bottom of the league. The only team below them was Oxford United. This, therefore, became an early season battle of the bottom two.

A win could have seen Argyle develop a four-point gap between themselves and the bottom of the league. That win, however, never looked like coming. After just four minutes, Ryan Edwards made a glaring error as he allowed the ball to slip under his foot in his own penalty area. That allowed former Pilgrim Jamie Mackie to give Oxford an early lead. Stuart O’Keefe skied an opportunity to level for the Greens, but it was a poor first half performance.

That was nothing, however, compared to the second half showing. Argyle barely got the ball into the opposition penalty area as Oxford truly dominated. They deservedly doubled their lead with just over 15 minutes to play as Curtis Nelson, another ex-Argyle player, pounced following a mix-up following a corner to slot the ball home. Yann Songo’o’s late red card compounded the misery for Argyle, who found themselves heading back to the foot of the table.

8 – Plymouth Argyle 0-3 Blackpool (7th March 2017)

Argyle were still well in the promotion hunt, and had the chance to close to within a point of top spot when Blackpool visited Home Park. The performance, however, was truly abject, as the visitors ran away with the points.

Adams decided Argyle would wear their away kit at home, bizarrely complaining that the green shirts clashed with Argyle’s surroundings during evening games. The brighter white kit didn’t help, however, as the visitors took the lead through Mark Cullen, and three minutes later the lead was doubled as Brad Potts turned the ball home. Things didn’t improve in the second half. A powerful strike from Jordan Flores, linked with Argyle in the previous January Transfer Window, ended the game as a contest after just 62 minutes.

All this occurred in the swirling rain of a chilly Tuesday night. A truly miserable day.

7 – Luton 5-1 Plymouth Argyle (17th November 2018)

When Argyle appointed Adams in 2015, it was widely accepted that the choice of who to appoint was between himself and Nathan Jones, a coach at Brighton when Argyle interviewed him. Argyle opted for Adams, whilst Jones ended up at Luton later in the season. Adams appeared to initially get the better of his previous competitor, leading Argyle to promotion in 2016/17 whilst Luton and Jones had to wait another year. When the sides met this season, however, things were very different.

Argyle, admittedly, were at a financial disadvantage. That wasn’t Adams’ fault. What he was to blame for, however, was the way he set his side up on the day. Luton’s diamond midfield has allowed them to dominate teams at Kenilworth Road all season, and Argyle did nothing to stop this, lining up with a 4-2-3-1 that was so easily pulled around by the Hatters. Elliot Lee and James Justin found the net, whilst James Collins netted himself a hat-trick. The 89th minute ‘consolation’ from Joel Grant was nothing of the sort. Argyle were well beaten.

6 – Accrington 2-1 Plymouth Argyle (12th March 2016)

Argyle were still in the hunt for automatic promotion heading into March, but some disappointing results, including a 1-0 reverse at Barnet, made the clash with fellow challengers Accrington very important.

Things didn’t start too badly for the Pilgrims in this one, and they took a first half lead when Jake Jervis looped a header over Ross Etheridge and into the net. They would hold that lead right up to the 85th minute, when the game turned on its head. Kelvin Mellor was shown a straight red card after fouling Billy Kee, who converted the resulting penalty. Things got worse in stoppage time when Shay McCartan headed Matty Pearson’s cross into the back of the Argyle net. The Greens had snatched defeat from the jaws of victory.

Argyle were still in the top three after the game, but momentum was against them. After a 1-0 defeat to Luton the following week, Argyle fell out of the promotion places. They wouldn’t get back in for the remainder of the season.

5 – Plymouth Argyle 1-5 Peterborough (25th August 2018)

Much like the Portsmouth game, this one was more painful to watch due to the previous match between the two sides. At the back end of the 2017/18 campaign, Argyle beat Peterborough 2-1 in a huge encounter. The game sent Steve Evans, a man so easy to hate, back home with his tail between his legs.

When Evans returned to Devon, however, things were very different. This game was another that demonstrated just how many steps Argyle had taken backwards between 2017/18 and 2018/19. It was a match lost by Argyle as much as it was won by Peterborough, as defensive errors plagued Argyle’s game. A shambles at the back allowed Jason Cummings and Matt Godden to net twice, and Siriki Dembele to add to the scoreline further. Ryan Edwards headed home for Argyle, but it added no respectability.

Evans and Peterborough left Home Park top of the league with a 100% record. For Argyle, a season of struggle beckoned.

4 – Exeter 2-1 Plymouth Argyle (2nd April 2016)

Defeats to local rivals are always tough to swallow. However, they happen – defeats in these circumstances do not necessarily make the game one of the worst of a manager’s reign, particularly one as long as Adams’. Indeed, Adams lost twice to Exeter during his time at Argyle, and only one of those matches makes this list. This game features not just because of the opposition, but because of the manner of the defeat, and the ramifications of it.

The first half was a cagey affair, but in the second Argyle took the lead as Jamille Matt took advantage of a loose ball in the penalty area to fire home. That had Argyle second in the ‘as it stands’ table, but with ten minutes to play, two vital points seemed to slip through their fingers. Ollie Watkins hit a hopeful looking shot from the edge of the area, and Luke McCormick was disappointingly beaten at his near post. It was the hosts’ first shot on target of the match.

And things got worse – deep into stoppage time Ollie Watkins had a shot from range again. He caught this one much better and found the top corner. Argyle had lost to their local rivals, and lost their place in the top three once more. It was a disastrous turn of events.

3 – Plymouth Argyle 2-3 Dagenham and Redbridge (23rd April 2016)

Crucial wins against Portsmouth and Leyton Orient left Argyle right in the promotion hunt with just three games to play. Just one point adrift of the top three, the visit of already relegated Dagenham & Redbridge to Home Park was surely a home banker.

After 41 minutes, however, Argyle’s promotion push was torn to pieces. First of all, Clevid Dikamona was allowed a free header from a corner to give the Daggers the lead. Soon that lead was doubled when a long-range Matty Cash strike found the top corner, and when Christian Doidge nodded in the visitors’ third before the break, the game was all but over.

Argyle fought back in the second half but it was never likely to be enough – they needed a win; a draw would not suffice. Peter Hartley’s header and Graham Carey’s sweet angled strike did nothing in the end other than adding a little respectability to the scoreline.

2 – Accrington 5-1 Plymouth Argyle (27th April 2019)

Another defeat at Accrington Stanley makes it into this top-ten. Had Argyle not lost at Wembley during Derek Adams’ reign, this match would have undoubtedly topped this list. Performance wise, it was surely the worst of the last four years. It was the match that ultimately made Adams’ position untenable, and indeed he was sacked a day after the final whistle.

Optimism was hardly high going into the game – Argyle were without a win in seven, and the lineup left a lot to be desired. Adams persisted with the poor midfield selection that saw his side struggle all season, and arguably Argyle’s player of the season Ruben Lameiras was dropped to the bench for a crunch relegation tie. That being said, nothing could have prepared the Green Army for what was to come.

In horrid conditions, Stanley ran riot. A Billy Kee penalty put them ahead, and Sean McConville scored two more before the break to end the game as a contest. In the second half, McConville completed his hat-trick, and Luke Armstrong added a fifth goal. Argyle’s stoppage time consolation came courtesy of an own goal from Mark Hughes. The result meant that Argyle went into the final game of the season against Scunthorpe knowing that even a win may not be enough to secure their League One survival. In the event, Argyle won but went down on goal difference.

1 – Wimbledon 2-0 Plymouth Argyle (30th May 2016)

Adams’ first full season at Home Park was full of ups and downs, but the Greens had a golden opportunity to end the season with the greatest of highs. A victory against Wimbledon at Wembley would have seen Argyle promoted to League One, with a win at the Home of Football.

On such occasions, it is imperative that the team show up and give themselves the best possible chance of securing victory. But whilst Wimbledon settled in and did just that, Argyle appeared to be overawed by the occasion. Their highlight of the first half was a Gregg Wylde cross that nearly found Jake Jervis. Yes, that was it. If it were a boxing match, then this was the equivalent of failing to lay a glove on the opposition.

With 12 minutes to play Wimbledon finally broke the deadlock. Lyle Taylor got to the ball before Kelvin Mellor could meet it with a diving header, and the Dons had control of the game. As Argyle pushed for a leveller, Wimbledon hit them on the break. Jordan Forster gave away a penalty, and Adebayo Akinfenwa converted.

The day was heart-breaking, and it meant Adams had failed in his objective to take Argyle out of League Two. He and the club would have to wait another year.