Leeds United, QPR got better of Bristol City in back to back windows | OneFootball

Bristol City must surely regret letting Luke Ayling and Luke Freeman join Leeds United and QPR respectively for six-figure fees in 2016 and 2017

Bristol City have remained a solid Championship outfit ever since their promotion from League One back in 2015, while the Robins have enjoyed their fair share of memorable moments over the years.

For example, the Ashton Gate faithful will never forget their club's historic run to the EFL Cup semi-finals back in 2017, which included an incredible 2-1 victory over Manchester United in the quarter-final, thanks to Korey Smith's 93rd-minute winner.

As well as on-field matters, Robins supporters have witnessed their club experience somewhat of a mixed record when it comes to the transfer market – for every Tammy Abraham, there has been a Lois Diony.

But two pieces of transfer business Robins fans would rather forget came in consecutive transfer windows, when Luke Ayling was sold to Leeds United during the summer of 2016, before Luke Freeman left for Queens Park Rangers in January 2017.

Leeds were the clear winners of Bristol City, Ayling deal

Full-back Ayling played a key role for the Robins side, who won the 2014/15 League One title, as he even notched four goals and two assists as he appeared in all 46 third-tier fixtures for his club.

He also made six appearances during the EFL Trophy run in the same season, which culminated in Wembley glory for the Ashton Gate side, as they emerged as 2-0 victors over Walsall in the final.

The defender subsequently made 33 appearances during the 2015/16 Championship season, in which the Robins successfully cemented their second-tier status.

But the West Country club chose to sell Ayling to Leeds for a fee of £200,000 in August 2016, then-manager Lee Johnson deeming him excess to requirements, and an Elland Road legend was born amid a development the Robins will surely now regret.

Indeed, the Arsenal academy product went on to give the Whites seven-and-a-half seasons of exemplary service, and most notably, helped the West Yorkshire side on their way to winning the 2019/20 Championship title.

After winning second-tier silverware with Leeds, Ayling was then ever-present in Marcelo Bielsa's side as the Elland Road outfit finished in an improbable ninth place in the Premier League.

He would remain in West Yorkshire for two more top-flight seasons before they suffered relegation back to the Championship at the end of a painful 2022/23 season.

Ayling would go on to join Middlesbrough on loan for the latter half of last campaign, before agreeing permanent terms with the Teessiders ahead of the current Championship season, as he left Elland Road with a legendary status.

Robins supporters must look at the full-back's exploits for Leeds with envy and will always wonder what could have been if he was able to stay at Ashton Gate for longer.

But no matter how much the Robins faithful will have regretted Ayling's West Country exit, the club made yet another transfer error just one window later as Freeman was allowed to join QPR for a fee of around £300,000 in January 2017.

Once again, the Ashton Gate outfit allowed a special talent to leave the club for a relatively low transfer fee, and would surely rue doing so in the years to come.

The midfielder produced a highly impressive return of seven goals and 17 assists during the club's aforementioned 2014/15 League One title-winning season.

He then went on to make seven goal contributions during the subsequent Championship season, which helped the Robins finish to a relatively comfortable 18th-place finish in the second tier.

But midway through the 2016/17 season, the Robins allowed him to move to QPR, and he went on to become a real asset for the Loftus Road side.

Freeman went on to notch five goals and 12 assists for the R's during the 2017/18 Championship campaign, before producing a return of seven goals and six assists during the following season.

His impressive exploits in west London were enough to convince Sheffield United to snap up his services ahead of the 2019/20 Premier League campaign as the Hoops made a healthy profit in a reported £5m deal.

It will have no doubt hurt Robins supporters to have seen Ayling lifting the Championship title during the same season as watching Freeman ply his trade in the top flight, in the knowledge that their club had previously sold the duo for a combined total of just £500,000.