Having first steadied the Oakwell ship following Lee Johnson’s exit in February, 2016 and then led the Reds to promotion just a few months later, the former defender had to cope with losing many of the exciting loanees who had played such a big role in that success.
Ashley Fletcher, who last summer joined Middlesbrough for £6.5m, returned to Manchester United as Ivan Toney, Josh Brownhill and Lloyd Isgrove did the same with their respective parent clubs to leave some big holes in a squad that also lost Alfie Mawson in a £5.5m deal a few weeks later.
Heckingbottom quickly set about plugging those gaps and, after kicking off 2017 with a 1-0 win at Nottingham Forest, Barnsley were just two places and four points adrift of the play-offs.
Then, though, came another flurry of departures in the January window as Conor Hourihane, Sam Winnall and James Bree moved on to leave the Reds’ chief needing to patch up his squad once again.
Replacing such quality is not easy at a club where every penny has to do the work of two so for the Reds to head to Reading tonight knowing victory will mean the top six is closer than the relegation zone is testament to the skills of their manager.
“We know what we are and we know where we have recruited players from and when,” said Heckingbottom. “It will always be a work in progress.
“Hopefully, as we go on through different windows, we can add to it and build, instead of weakening. That has to be our aim as a club.”
Tonight will bring Barnsley’s second trip of the year to the Madejski, February’s goalless draw being one of just two home outings during the final three months in which the Royals dropped points.
Eventual champions Newcastle United were the other side to leave Berkshire with a draw, but it has been a different story this time around with Jaap Stam’s men having suffered a major play-off hangover following last May’s Wembley defeat to Huddersfield Town.
Reading sit a place below Barnsley in the table on goal difference, but Heckingbottom insists no one should underestimate the size of the task facing his players tonight.
“Reading are very similar to last season,” he said. “It has just been the results. If they had won a couple more games then everyone would have been talking about them in the same vein as last season. Look at the Sheffield Wednesday game (at the weekend, which finished 0-0).
“They dominate the ball like last season and the game in terms of possession. If they win that 1-0 then it is the same as last season and people are saying, ‘What a good side Reading are’.
“They have looked to strengthen with the recruits they have brought in so everything I have seen about them tells me how tough it is going to be.”
Mamadou Thiam may return after a back problem, but Isgrove, signed permanently from Southampton last summer, remains out with a swollen knee. Adam Hammill is suspended after collecting his fifth booking of the campaign in the weekend defeat to Leeds United.
Ryan Hedges, following his impressive cameo from the bench in that 2-0 loss, is hoping to be handed a recall as Barnsley chase what would be only their 11th league win in 2017 from 42 outings.
“To lose a derby like we did (on Saturday), said the 22-year-old, “we were all bitterly disappointed. Everyone was deflated, but now we have a chance to put it right against Reading.
“For me, it has been a bit of an up-and-down season. The highs include starting the season so well and the Wales call-up, but I have also not been playing as much as I want to.
“Hopefully, though, I can put my name forward from the performance against Leeds to try and get a starting role again.
“Every winger who has played has done a really good job. It is probably one of the strongest positions at the club, meaning you just have to wait for your turn and take it when the gaffer says you are starting.”
Hedges’s international debut for the Wales senior side came earlier this month in the 1-1 draw with Panama. He added: “It was a really proud moment for me, a big personal achievement, one I had been dreaming of when coming through the ranks of the Under-19s and 21s.
“To get my first senior cap gives me a lot of confidence. I want to take it into my form at Barnsley. I want to carry on playing well and getting goals.”
Last six games: Reading LWWLDD Barnsley DWWDLL.
Referee: D Bond (Lancashire).
Last time: Reading 0, Barnsley 0; February 11, 2017; Championship.