Midlothian
Council area of Scotland
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| April 2024 | Replaced as technical director by Jason Wilcox, but retained a key role in the football leadership team at Manchester United. |
| July 2023 | Twin sons Jack and Tyler transferred from Manchester City academy to Manchester United academy. |
| February 2023 | Jack and Tyler Fletcher played against each other in a match, with Jack having been selected for the England under-16 squad. |
| 2022 | Promoted to Scottish League Two and reached the second round of the Scottish Cup, losing to Sauchie Juniors. |
| 2022 | Bonnyrigg Rose won promotion to Scottish League Two, entering the Scottish Professional Football League for the first time, and changed their name from Bonnyrigg Rose Athletic to Bonnyrigg Rose. |
| August 2022 | Twin sons Jack and Tyler selected for the Scotland under-16 squad. |
| 2021 | Competed in the Lowland League, finishing 1st. Reached the third round of the Scottish Cup, losing to Alloa Athletic. |
| 2021 | Bonnyrigg Rose won the Lowland Football League, securing promotion. |
| March 2021 | Becomes technical director at Manchester United. |
| January 2021 | Appointed to Manchester United's first-team coaching staff. |
| 2020 | Narrowly lost to Scottish Championship side Dundee in the Scottish Cup after leading twice, with the match going to extra time and ultimately ending in defeat. |
| 2020 | Defeated Bo'ness United 5-2 in the Scottish Cup Second round, with Lee Currie scoring a hat-trick of penalties within 10 minutes. |
| October 2020 | Returns to Manchester United as a coach, working with under-16s players. |
| May 2020 | Acknowledged he 'probably' wouldn't play again, citing his medical condition (ulcerative colitis) and higher COVID-19 risk. |
| May 2020 | Wayne Rooney acknowledged Fletcher as a vital member of Manchester United's successful 2006-2009 team, placing him on par with key players like himself, Cristiano Ronaldo, and Carlos Tevez. |
| 2019 |
Shawfair
Continued progression of commercial and house building phases in the Shawfair development.
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| 2019 | Competed in the Lowland League, finishing 2nd. Reached the fourth round of the Scottish Cup, losing to Clyde. The season was curtailed due to the COVID-19 pandemic. |
| 2019 | Bonnyrigg Rose F.C. was promoted to the Lowland League after winning the East of Scotland Football League and gaining Scottish Football Association (SFA) membership, replacing Whitehill Welfare. |
| 2019 | In their first Scottish Cup as a licensed team, defeated Highland League sides Fraserburgh and Buckie Thistle, and won against Scottish League One side Montrose 2-1 at New Dundas Park. |
| November 2019 | Stated he had not officially retired from playing and was not yet ready to begin a career in management. |
| November 2019 | Darren Fletcher expressed his aspiration to pursue a career in football management. |
| June 2019 | Accepted as a member of the Scottish Football Association, which would allow automatic qualification for the Scottish Cup. |
| 2018 |
Shawfair
First phases of commercial and house building were progressed in the Shawfair development.
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| 2018 | Bonnyrigg Rose F.C. won the East of Scotland League Conference B, SJFA East Region Super League, and Fife & Lothians Cup. |
| 2018 | Bonnyrigg Rose competed in the East of Scotland League Conference B, finishing 1st and reaching the first round of the Scottish Cup, where they lost to Deveronvale. |
| 2018 | Participated in the inaugural Shaun Woodburn Memorial Cup, established in memory of former player Shaun Woodburn. |
| November 2018 | Robbie Horn returns to manage Bonnyrigg Rose F.C. after previously resigning in August 2017. |
| October 27 2018 | Scored the only goal of the game against Bristol City. |
| March 2018 | At a special general meeting, club members voted to apply for membership in the senior East of Scotland Football League. |
| 2017 | The club was runner-up in the SJFA East Region Super League. |
| 2017 | Leaves West Bromwich Albion after making 97 appearances. |
| 2017 | Darren Fletcher represented Scotland national team, making 3 appearances with no goals scored |
| October 28 2017 | Scored his first goal for Stoke City in a 1-0 win away at Watford. |
| August 2017 | Robbie Horn resigns from managing Bonnyrigg Rose F.C. to take the managerial position at Berwick Rangers. |
| August 12 2017 | Made his debut for Stoke City in a 1-0 loss at Everton, playing the full 90 minutes. |
| June 1 2017 | Signed a two-year contract with Stoke City, effective from the expiration of his West Bromwich Albion contract on 1 July. |
| February 4 2017 | Played his 300th Premier League game against Stoke City, with Sir Alex Ferguson praising him as a 'fantastic professional and fantastic human being'. |
| January 21 2017 | Scored his second goal of the 2016-17 season in a 2-0 win against Sunderland. |
| 2016 | Bonnyrigg Rose F.C. played Hibernian at Tynecastle Stadium in the Scottish Cup, resulting in an 8-1 defeat in front of 5,000 traveling supporters. |
| 2016 | In their most successful Scottish Cup campaign, Bonnyrigg defeated Glasgow University, followed by a record-breaking 14-0 victory over Burntisland Shipyard. They progressed through wins against Turriff United and Cove Rangers, and notably eliminated Dumbarton of the Scottish Championship after a replay. |
| 2016 | Darren Fletcher represented Scotland national team, making 7 appearances with no goals scored |
| November 21 2016 | Scored his first Premier League goal of the 2016-17 season in a 4-0 win against Burnley. |
| September 2016 | Resumed the captaincy of Scotland national team after Scott Brown temporarily retired from international football. |
| 2015 | Bonnyrigg Rose F.C. won the SJFA East Region Super League. |
| 2015 | Darren Fletcher represented Scotland national team, making 3 appearances with no goals scored |
| 2015 | Named West Bromwich Albion Player of the Year |
| December 28 2015 | Scored his second goal for West Brom in a 1-0 win against Newcastle United. |
| October 2015 | By the international break, had not missed a minute of Premier League football, symbolizing his full comeback from illness-disrupted seasons. |
| September 2015 |
Shawfair
Shawfair railway station was opened on the newly created Borders Railway, connecting the new town centre with Edinburgh city centre.
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| June 2015 | Robbie Horn begins managing Bonnyrigg Rose F.C., having previously been a player and assistant manager at Berwick Rangers. |
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