He has enjoyed a brilliant four years so far at the Reds but has been struggling this season to emulate his form of previous years.
Lolley has been on one hell of a journey to even get to this point. From University degrees to Premier League football he certainly has had a fairytale career.
Unlike the rest
However, growing pains halted his development and was subsequently pushed to the fringes. Despite this, the club didn't want to release Lolley because of his potential, and in a bid to give the Villa fan a better chance of gaining a scholarship, he was held back a year and placed in the Under 15s.
Lolley agreed to the transition and spent a few months with the younger age group before he left the club and decided to focus on his A-Levels.
Aged 18, Lolley went to the University of Central Lancashire to study Sports Coaching whilst playing for local non-league side Littleton FC. This was the start of his meteoric rise to the top of English football. He made 83 appearances for the Worcestershire side scoring a staggering 88 goals.
After a couple of impressive years at his local side, the 20-year-old bagged a move to a high profile non-league side...
The first step up the ladder
After a successful trial, Lolley joined Conference Premier side Kidderminster Harriers on an initial one-year deal. It didn't take the former Birmingham man to get off the mark for his new side. In just his second appearance against Chester, he bagged his first goal for Kiddy in a 3-1 win.
By January, Lolley had racked up an impressive nine goals in 21 league starts including a hat-trick in his last league game against Salisbury City. The Harriers impressive form saw them reach the FA Cup third round, where they faced League One Peterborough United. Following a resolute performance, Kidderminster secured a 0-0 draw ensuring a replay at London Road, a game that would change the former Blues winger's career.
His late winner sealed a 3-2 win for the fifth tier side which prompted a bid from the losing side just days later. However, he rejected the deal and instead joined Championship side Huddersfield Town for a fee in the region of £300,000.
One step closer...
His signing for the Terriers meant that Lolley was just one division away from every young boy's dream of playing in the Premier League. After joining the Yorkshire side, it was important that the winger bided his time and took his opportunity when it came his way.
After multiple impressive cameo appearances off the bench, manager Mark Robins handed the youngster's first start against Watford in the final game of the 2013/14 season. With no pressure on him, Lolley ran the show scoring once and laying on two assists for his new teammates leading them to a 4-1 victory.
Lolley first secured a consistent place in the Terriers starting 11 in the 2016/17 season. The wide man made 25 league starts with a further seven off of the bench. He accumulated a respectable total of four goals and two assists in the blue and white stripes of Huddersfield until injury hampered his participation in the Terriers historic campaign.
Under German manager David Wagner, Huddersfield defeated Reading in the play-off final on penalties and secured promotion to the Premier League for the first time in their history, but Lolley rarely featured that season with just eight league starts.
Wagner gave Lolley a rare start in the top flight against West Ham United and the nimble winger took his opportunity with both hands. He cut in from the right-hand side and curled a lovely effort into the far corner but it wasn't enough to stop his team from falling to a 4-1 defeat. This proved to be his last game for Town.
Terriers to Trentside
After a brief spell at the pinnacle of English football, Lolley dropped back into the second tier signing for Nottingham Forest for a reported £500,000. The move allowed him to be a first-team regular under then-manager Aitor Karanka. Four games into his Forest career, Lolley scored in the 5-2 rout at Queens Park Rangers and followed it up a week later by scoring against his former side Birmingham in another win for the Reds.
Lolley featured in 16 out of 17 remaining games towards the back end of the 2017/18 season with many Forest fans impressed with his instant impact.
Season of his career
The summer of 2018 was a record-breaking one for Forest. The Reds smashed their transfer record by signing Joao Carvalho from Benfica for a fee believed to be in the region of £13.2 million. The Portuguese Under 21 international was joined at the club by fellow Portugal youngsters Gil Dias and Diogo Goncalves.
Despite the high profile arrivals, Lolley maintained his place in the starting 11 and scored his first goal of the campaign against Birmingham once again. His most impressive performance of the 18/19 season came against his boyhood club Aston Villa at Villa Park in November. The Reds drew 5-5 against the side from the West Midlands, with Lolley assisting four and scoring the other which ending up being voted Forest's goal of the season.
The winger's impressive displays throughout the season saw him claim the PFA Player of the Month award for October after he scored three goals and claimed two assists. Lolley was again nominated for the award the following month after two goals and four assists in November. After an impressive first half of the season, Lolley signed a new four-and-a-half-year deal that would see him stay at the club until 2023.
In his first full season with the Reds, Lolley featured in every single game and impressed throughout grabbing himself 11 goals and 11 assists. To cap off a memorable season, the winger was crowned player of the season after claiming 56% of votes.
Transfer gossip was always going to be inevitable after such a successful season. Just days into the window, the rumour wheel started spinning with Villa being linked with a £15 million move for the wideman after their promotion to the top flight.
Continuing where he left off
After the Reds fended off interest from multiple Premier League clubs, Lolley became a key man under new boss Sabri Lamouchi. For the third season in a row, the former Blue scored his first home goal of the season against the side he once represented as a teenager.
His hard work and passion for the Forest faithful never goes unnoticed. After the Reds picked up all three points against Barnsley, the "Love you Lolley" meme was created with the winger acknowledging the post on his Twitter page along with fellow first-team player Joe Worrall.
His star performance in the 2019/20 season came against Leeds United where Forest beat the table-toppers 2-0 at the City Ground with the winger assisting Tyler Walker in the final minute to seal an impressive victory.
His consistent performances throughout the season led to him racking up nine goals and nine assists in what proved to be a disappointing end to a highly disrupted season where the Reds famously missed out on the top six on the final day after falling to a 4-1 defeat to Stoke City.
Mysterious injury problems
Towards the back end of last season, Lolley was missed a few games whilst only being fit enough for the bench in a couple more. At the time it was put down to "shin splints".
However, in a recent interview with Nottinghamshire Live, Lolley confirmed it was something a little more serious than that, he said:
"It's a problem I've had my whole career called muscle compartment syndrome. It's not shin splints. The first few games after lockdown was brilliant but then I just sort of broke down."
Muscle compartment syndrome is a potential serious condition that is usually caused by bleeding or swelling within a group of muscles.
In an attempt to be fully fit for these start of the 2020/21 season Lolley confirmed that he had treatment to try and ease the pain.
"In the summer I had to get injections and it takes quite a while for it to happen. I tried to rush back," he said.
"I've always felt a duty to try to play for this club. I've always tried to work my hardest to be available for every game."
Lolley's first tough spell
This season has been a tough one for Lolley. He has started 14 times with a further 10 appearances off the bench. He has only managed one goal and two assists which by his standards is really poor.
Despite this, the Reds fanbase remain fully behind Lolley and recognise the struggles he's had this season and also the change in management.
Manager Chris Hughton's first signing in charge of Forest was winger Anthony Knockaert on loan from Fulham. The pair previously worked together at Brighton in which they gained promotion to the Premier League.
Knockaert's good form has been another contributing factor to Lolley's time on the bench, however things are looking up for the 28-year-old. The injury to fellow winger Sammy Ameobi has given the former Huddersfield man a route back into the starting 11.
In the recent game away at Wycombe Wanderers, Lolley came off the bench to set up Knockaert to finish off the game. The trademark shoulder drop and cross was a glimpse of the Lolley that Reds fans know and love. Hopefully this is the start of a great end to a disappointing season for the fan favourite!