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Grimes had minor wrist surgery in the 2019/20 off-season, missing just 10 days of training in late November for the recovery. In mid-December, teammate Alex Rance announced a shock retirement, reconfirming Grimes' place as the club's premier defender following his outstanding 2019 season played in Rance's injury-absence. Grimes featured in each of the club's two pre-season matches in March before contributing five marks in round 1's win over Carlton. The match was played under extraordinary conditions, the first of what had been announced would be a shortened 17-round season imposed on the league as a result of the rapid progression of the coronavirus pandemic into Australia. Due to public health prohibitions on large gatherings, matches that season were to be played without crowds in attendance and with quarter lengths reduced by one fifth in order to reduce the physical load on players who would be expected to play multiple matches with short breaks in the second half of the year owing to the likelihood of an extended break in play that season. Within three days of the round 1 win however, the AFL Commission suspended the season for a period of at least 10 weeks after multiple states enforced quarantine conditions on their borders.

Grimes plays as a lock-down defender, capable of directly matching up on tall and small forwards. He is notable for the foot-speed to contain small opponents and the spoiling prowess to effectively defend key position forwards. After previously being described by Richmond head coach Damien Hardwick as the Robin to teammate and five-time All-Australian Alex Rance's Batman, Grimes ascended to become one of the league's best defenders with Rance's knee injury and subsequent retirement in 2019.

Outside of football, Grimes and his partner Elisha are the co-owners of Mount Macedon Winery. The pair were married at a ceremony on the winery grounds in November 2019.

In the 2018/19 off-season, Grimes underwent minor finger surgery but did not miss any training as a result. In mid-January 2019 he suffered a broken nose during a training session collision with teammate Nathan Broad. Grimes immediately returned to training after surgery to realign the nose, wearing a protective face mask for more than a month while the injury continued to heal. He played in each of the club's two pre-season matches before opening the season with a round 1 win over Carlton. Prior to the match, Grimes had been labelled by Fox Footy commentator Nick Riewoldt as "one of the best lockdown defenders in the competition" and highlighted as one of the league's most irreplaceable players. It was Richmond backline leader and five time All-Australian Alex Rance who would ultimately need to be replaced however, after suffering a torn ACL in that match which would rule him out for the entirety of the season and leave Grimes to lead the club's backline group. In round 2, Grimes received a one match suspension for striking Collingwood forward Jamie Elliott. When he returned in round 4, AFL Media named Grimes a key candidate to captain the side in the absence of all three members of Richmond's leadership group, though he would eventually be passed over for the role in favour of veteran Shane Edwards. He lead in another way, taking six marks in the final quarter in a best-on-ground performance that earned him his first three Brownlow Medal votes and that senior coach Damien Hardwick said "won the match for (Richmond)". Following that match, AFL Media labelled Grimes the best one-on-one defender in the league and that he had taken the mantle of the league's best defender from the injured Rance. He picked up two votes in the coaches association player of the year award in round 6 before adding more votes in three consecutive matches between round 8 and 10. In that round 8 win over Fremantle, Grimes gathered a career-best 26 disposals. Halfway through the year, Grimes was named in ESPN's mid-year All-Australian team and named by Fox Footy as a contender for the end of year honour. In round 18, Grimes earned two coaches votes for a performance in a win over Port Adelaide that also saw him named to AFL Media's Team of the Week. He was again named in that team the following week but did so along with best on ground honours with nine coaches votes in round 19's win over Collingwood. For that effort which included an equal career-high six intercept marks, Grimes was labelled by the Herald Sun as a likely All-Australian selection. In the five matches between the bye and that point, Grimes had lost just two of 21 one-on-one contests, while averaging a loss percentage of 16.4 across the length of the season. He was also picked by 3AW commentator Matthew Lloyd as the best key position defender in the league. During a match against West Coast in round 22, Grimes left the field with an ankle injury after landing awkwardly in a marking contest. He ultimately played out the match and despite some limited training during the week that followed, lined up in round 23's win over the Brisbane Lions where he restricted Charlie Cameron to just seven disposals and earned another selection to AFL Media's team of the week. Grimes concluded the regular season ranked 10th in the league for one percenters and 12th for intercepts, earning selection in The Age and the Herald Suns teams of the year. He earned an official honour with selection to the All-Australian team for the first time and was voted by the players association as the league's most courageous player. After nine straight wins to finish the home and away season, Grimes was set for another contest directly opposed to Charlie Cameron in a qualifying final against the Brisbane Lions at The Gabba. He produced a "dominant performance" to restrict Cameron to a single goal, helping Richmond win through to a home preliminary final against Geelong. Grimes received four coaches votes as the third best player on the ground during the qualifying final, but was also fined $1000 by the league for staging for a free kick when pushed by an opposition player in an off-the-ball incident in the first half of that win. In the preliminary final, Grimes was reliable in defence and helped his side through to a second grand final appearance in three seasons. In the grand final, Grimes held Coleman Medalist Jeremy Cameron to a single goal, and was part of the Richmond defence that kept the Giants to 25 points, their lowest score in the club's eight-year history and the lowest score by any team in a VFL/AFL grand final since 1960. Grimes finished what AFL Media called "a career-defining year" by winning a second AFL premiership and placing third in the club's best and fairest count, his best finish to date. He was also named as the league's best defender and 20th best player overall in the Herald Sun chief football reporter Mark Robinson's list of the league's best players in 2019.

For the first time in his career, 2017 saw Grimes enter the season injury-free after also having a full and uninterrupted pre-season. He played a key role in the club's round 2 win over Collingwood, blanketing small forward opponent Alex Fasolo and keeping him goalless. Grimes was one of the club's best in round 5 too, recording an equal team-high seven tackles along with six intercepts and eight one percenters and earning himself two votes in the Coaches Association's Player of the Year award. Between rounds 10 and 15 he did not concede a single goal on his direct opponent, a figure that helped contribute to Champion Data ranking Richmond's defence as the fourth best in the competition after 14 rounds. In July Grimes' season was described by The Age's Michael Gleeson as "the best and most consistent" of his career. He finished the home and away season having played all 22 matches for the first time in his career while Richmond qualified for the finals double chance for the first time in 16 years. Grimes and the Richmond defence held Geelong to just five goals in the qualifying final before dispatching of the GWS Giants in a home preliminary final to earn a grand final berth. There they faced the minor premiers Adelaide, who boasted the most effective forward line in the competition that season. It was Grimes' club who would win the day however, as he nullified the Crows' Eddie Betts and became a premiership player in his 104th career match. He was later named in the back pocket in the AFL Media Team of the Finals. He finished the year having recorded the league's sixth best defensive rating among players classed as general defenders and winning the sixth best percentage of defensive one-on-one contests (43 per cent). In Richmond's end of season awards he received the Francis Bourke award as selected by his teammates for most embodying the qualities of awareness, unitedness, relentless and discipline. Grimes was also awarded the Kevin Bartlett medal for a fifth-placed finish in Richmond's best and fairest award and placed third and fourth at the club for one-percenters and intercept possessions respectively.

By the beginning of 2016 Grimes had established himself as a key member of the club's defensive unit. For the second straight season he would play in rounds 1 and 2 before a hamstring injury would keep him out of round 3 action. What was forecast as a two-week injury turned into a five-week one however, as he did not return to senior football until round 8's match against Sydney. After playing in three consecutive matches Grimes was a late out in round 11, pulling up poorly in the pre-game warm up and causing a late change as a result. The effects were minor however and he would play without trouble the following week. In fact, he played in each of the club's final 11 matches of the season and recorded double digit disposals in all matches and an average of 4.5 marks over the period. Grimes also recorded a career high eight tackles in round 16 against the Western Bulldogs. He placed equal seventh in the club's best and fairest count in what was his best career season to that point.

Entering 2014 Grimes has shed three kilograms of body mass, adjusting for a change in role from key defender to small defender. Grimes was also left out of the club's leadership group that season. His first match of the season came in the club's re-match with the previous year's finals opponent Carlton, in round 2, 2014 at the MCG. He remained in the club's senior team for the following four matches before being omitted from the side ahead of round 7. Grimes returned to senior football in round 10. He missed a single match in round 12 with a toe injury but otherwise played in every remaining match that season as well as in another elimination final. At season's end he had played a career-best 19 games and placed 11th in the club's best and fairest award.

Grimes spent part of the 2014/15 pre-season looking for a mental edge, reading extensively about mindfulness in competitive sport and serving as the catalyst for the introduction of a meditation program which when fully implemented two years later would become a key component of the club's success. He completed that pre-season injury free and entered round 1 playing as Richmond's third tall defender. By round 3 he had re-injured his hamstring, sitting out three weeks of football at AFL level as a result. He returned in round 6 against North Melbourne, and this time stayed in the side for 13 consecutive matches. Grimes was subbed out at half time of Richmond's round 19 match with Adelaide, after suffering a minor hamstring strain earlier in the match. He would miss two matches as a result, before returning in round 22 against Essendon at the MCG. At season's end he had played in 18 matches including a losing elimination final. He placed equal ninth in the club's best and fairest award that year, polling votes in 17 of his 18 matches that season.

The 2013 pre-season started ominously for Grimes, with the defender failing to travel to the team's pre-season camp in Cairns on account of soreness in his left leg. Later revealed to be a small split in his hamstring tendon, he would again require surgery to repair the damage. Days later he was added to the club's leadership group, serving under newly appointed captain Trent Cotchin. Grimes played his first match of the season in round 2 against St Kilda at the MCG. He played in five consecutive matches before sustaining a foot fracture in round 6 against Geelong. After 15 weeks on the sidelines, Grimes returned to AFL football in round 21. He remained in the side for the final three matches of the home and away season before playing in his first career final, a losing elimination final against Carlton at the MCG.

Grimes returned to football fully fit in 2012, playing in the club's round 1 match against Carlton at the MCG. He earned an AFL Rising Star award nomination in round 3, for an 18 disposal and nine mark performance against Melbourne. In round 7 he recorded three career-highs with 13 marks, 24 disposals ans six rebound 50s in a match against Sydney. Grimes again suffered a major hamstring injury in the club's round 8 Dreamtime match against Essendon. He missed five weeks of football to rehabilitate the injury, before returning in round 14 to face Adelaide at AAMI Stadium. Despite recording a team-best 10 marks in the match, Grimes re-aggravated the injury and required further treatment as a result. He traveled to Germany soon after to be treated by renowned soft tissue expert Hans-Wilhelm Müller-Wohlfahrt. Part of his treatment involved injections of calf blood extract actovegin directly into the affected muscle together with 200 injections into his lower back over the course of a single week. He did not return to senior football that season, finishing his season with just nine matches played.

In 2011 Grimes again started the season playing reserves grade football, this time for the first two matches of the season. However, when fellow defenders Alex Rance and Luke McGuane were ruled out due to suspension in round 3, Grimes was called to take a key defensive role in the Richmond AFL side. In his first match of the season and just his second career match, he recorded 15 spoils, equaling an AFL record at the time. After five rounds he held an average of 13 spoils per game, and the number one ranking in the league. He played in the next four consecutive matches before a severe hamstring injury sustained in round 9's Dreamtime at the 'G match saw Grimes sidelined for the remainer of the 2011 season. At year's end he had played a total of seven matches and held averages of 12.6 disposals and 3.8 marks per game.

Grimes was drafted by Richmond with the club's first pick and the second selection overall in the 2010 AFL Pre-Season Draft.

He played the majority of his first season at reserves level with Richmond's VFL affiliate team, Coburg. Included in that year were multiple games with Coburg's reserves team, a full two levels below AFL football. Overall his footballing was minimal that year, with an eye injury keeping him from playing most of the season. Grimes eventually made his AFL debut late in 2010, in round 22 against Port Adelaide at Docklands Stadium.

Grimes grew up on a hobby farm in Panton Hill, 32 kilometres north-east of Melbourne. He played junior football at Hurstbridge in the Northern Football League before playing TAC Cup football with the Northern Knights in 2009.

Grimes went un-drafted in the 2009 AFL National draft despite assurances from Hawthorn and Melbourne that they would select him with third and final round picks, respectively. He was offered the chance to train with Richmond in the following weeks with the expectation that the club would officially select him in the December pre-season draft.

Dylan Grimes (born 16 July 1991) is an Australian rules footballer who plays for the Richmond Football Club in the Australian Football League (AFL). He is a two-time premiership player with the club, winning in 2017 and 2019. In 2019 he was also selected in the All-Australian team.