In punching distance of the Championship’s automatic promotion spots after his first few months, what followed was a manic tumble both on and off the field which saw a mammoth points deduction and off the field chaos drift over the club.
Though it came before the mass exodus of players and huge squad transitions felt in the last two summers, Monk kicked off a changing room turnover in his time, with 13 players walking through a door with his name above it.
Of those 13 players only three remain at Hillsborough and only one still plays at the level at which they were signed – the Championship.
Featuring free agents, players to have hopped around the world since and one stationed out in the Malaysian leagues, let’s take a look at how they’re getting on.
1. Alessio Da Cruz
Brought in at the end of a slow-moving January 2020 transfer window - Monk's first since his September appointment - Da Cruz was something of a rogue addition on loan from Parma. He'd spent the first half of the season at Ascoli in Serie B and played 15 times for the Owls, failing to score. Since? He's played for four clubs in four countries - Groningen in Holland, Santos Laguna in Mexico, Vicenza in Italy - all on loan - and now KV Mechelen in Belgium, where has two goals in 13 appearances. Photo: Clive Brunskill
2. Connor Wickham
His third and least successful loan stint with Wednesday came in the second half of the 2019/20 campaign and returned two goals in 13 as he battled injury. He returned to injury nightmare at parent club Crystal Palace and later signed for Preston North End on a free transfer but has his stint cut short as fitness issues reared their head again. MK Dons was next, in the final strait of last season. He's now in League One with Forest Green Rovers, where he has eight in 18. Photo: Dan Mullan
3. Jack Marriott
Another forward who arrived with fitness concerns, this time for the points deduction season of 2020/21, Marriott struggled his way through the campaign making only 13 appearances.. and going goalless. He signed for his old club Peterborough United having been released by Derby County and either side of more injury woe has done OK, scoring nine Championship goals last season before grabbing seven in 26 this season. Photo: Clive Brunskill
4. Ryan Galvin
Seen as one of the brightest young players at the club, Galvin is one of the few Monk signings still at S6. Brought across from Wigan in January 2020, the left-sided defender has made four cup appearances for the seniors. Now 21, he is out on loan at Maidstone United after a previous loan stint at Gloucester City. Photo: SWFC