Arsene Wenger

First Arsenal signing: Nicolas Anelka (from PSG for £500,000, 1997)
Most expensive career signing: Mesut Ozil (Real Madrid to Arsenal for £42.5m, 2013)

First career signing
Of the more than 100 players Arsene Wenger has signed throughout a 33-year managerial career, the distinction of the Frenchman’s first ever signing belongs to Jean-Luc Arribart. Wenger signed the defender, who he actually met and befriended at university in France, for Nancy in 1984.

Eddie Howe

First Bournemouth signing: Ryan Fraser (from Aberdeen for £400,000, 2013)
Most expensive career signing: Jordon Ibe (Liverpool to Bournemouth for £15m, 2016)

First career signing
Harry Arter and Marc Pugh, still with Eddie Howe and now seasoned members of his Bournemouth squad, were the second and third signings of his managerial career in 2010. But they were both marginally beaten to the number one spot by Liam Feeney, signed from Salisbury in February 2009 for just £34,000. How times change.

Chris Hughton

First Brighton signing: Tomer Hemed (from Almeria for £1.1m, 2015)
Most expensive career signing: Ricky van Wolfswinkel (Sporting to Norwich for £8.5m, 2013)

First career signing: Imagine enjoying a relatively successful 16-year playing career, earning 53 caps for your country, then branching out into coaching, managing four clubs and carving out a highly-respected reputation, but always knowing that your first signing ever was Mike Williamson for just under £1m from Portsmouth in January 2010.

Sean Dyche

First Burnley signing: Michael Kightly (from Stoke for £1.6m, 2014)
Most expensive career signing: Robbie Brady (Norwich to Burnley for £13m, 2017)

First career signing: Sean Dyche has made 24 permanent signings in his managerial career since taking over at Watford in 2011. His first was former Tottenham winger Mark Yeates, purchased from Sheffield United for £380,000 in July 2011.

Antonio Conte

First Chelsea signing: Michy Batshuayi (from Marseille for £33m, 2016)
Most expensive career signing: Michy Batshuayi (Marseille to Chelsea for £33m, 2016)

First career signing: What do you mean you’ve never heard of 37-year-old Italian journeyman midfielder Daniele De Vezze, signed by a probably balding Antonio Conte for Bari in June 2008.

Ronald Koeman

First Everton signing: Maarten Stekelenburg (from Fulham for £850,000, 2016)
Most expensive career signing: Yannick Bolasie (Crystal Palace to Everton for £25m, 2016)

First career signing: You might remember the name Bob Peeters, whose two achievements in life are coaching Charlton for 28 games from 2014 and being the first signing ever made by Ronald Koeman, then manager of Vitesse in 2000.

David Wagner

First Huddersfield signing: Elias Kachunga (from Ingolstadt on loan, 2016)
Most expensive career signing: Christopher Schindler (1860 Munich to Huddersfield for £1.8m, 2016)

First career signing: Cast your minds back to the heady days of June 2016, when little-known one-hit wonder Drake topped the British music charts, Leicester were one month removed from becoming Premier League champions, and Jeremy Corbyn was an absolute joke. Ah, good times. Oh, and David Wagner swooped to sign Elias Kachunga on loan from Ingolstadt. He might have a bit more money to spend this summer.

Jurgen Klopp

First Liverpool signing: Marko Grujic (from Red Star Belgrade for £5m, 2016)
Most expensive career signing: Sadio Mane (Southampton to Liverpool for £34m, 2016)

First career signing: When Spasoje Bulajic likes to brag to his family and friends, he regales them with accounts of how he was named 1997 Slovenian Youth Footballer of the Year and 1998 Slovenian Footballer of the Year. And when he wants to really impress people, he tells them how he was Jurgen Klopp’s first ever signing as Mainz manager for £43,000 in July 2002.

Pep Guardiola

First Manchester City signing: Ilkay Gundogan (from Borussia Dortmund for £22.9m, 2016)
Most expensive career signing: Zlatan Ibrahimovic (Inter Milan to Barcelona for £40m plus Samuel Eto’o, 2009)

First career signing: As if to really hammer home just how different Pep Guardiola’s coaching beginnings were in comparison to his Premier League counterparts, his first ever signing as a manager was £11.2m Sevilla midfielder Seydou Keita.

Jose Mourinho

First Manchester United signing: Eric Bailly (from Villarreal for £30m, 2016)
Most expensive career signing: Paul Pogba (Juventus to Manchester United for £89.3m, 2016)

First career signing: Here’s a quiz question for you: Which four players have been signed by Jose Mourinho more than once? Three are obvious, with Paulo Ferreira, Tiago and Ricardo Carvalho all very much synonymous with the Portuguese from his time at Porto, Chelsea, Inter Milan and Real Madrid. But the fourth was purchased during his seven-month tenure at União de Leiria. Mourinho would go on to bring Maciel with him to Porto.

Rafael Benitez

First Newcastle signing: Mats Selz (from Gent for £5m, 2016)
Most expensive career signing: Gonzalo Higuain (Real Madrid to Napoli for £34.5m, 2013)

First career signing: Mats Selz was his first at Newcastle. Marco Asensio was his first at Real Madrid. Dries Mertens was his first at Napoli. Marko Livaja was his first at Inter Milan. Josemi was his first at Liverpool. Salva Ballesta was his first at Valencia. But Rafael Benitez popped his transfer cherry all the way back in 1995 by bringing Alberto Marcos Rey with him from Real Madrid to Valladolid.

Claude Puel

First Southampton signing: Nathan Redmond (from Norwich for £10m, 2016)
Most expensive career signing: Lisandro Lopez (from Porto to Lyon for £20.5m, 2009)

First career signing: Few managers can claim to have a more illustrious first signing ever than Claude Puel. His Monaco side was the first venture into Europe for Rafael Marquez in 1999, with the Mexican joining from Atlas for £3.8m.

Mark Hughes

First Stoke signing: Erik Pieters (from PSV for £3m, 2013)
Most expensive career signing: Robinho (from Real Madrid to Manchester City for £32.5m, 2008)

First career signing: Some managers are defined by the signings they make. Somehow, it would feel weird if the first purchase Mark Hughes ever made as a boss was not that of Robbie Savage. In his first club post after starting life as a head coach with Wales, Hughes signed Savage for just over £3m from Birmingham for Blackburn in 2005.

Paul Clement

First Swansea signing: Luciano Narsingh (from PSV for £4m, 2017)
Most expensive career signing: Bradley Johnson (Norwich to Derby for £6m, 2015)

First career signing: For a man whose managerial career started only two years ago, Paul Clement should perhaps be forgiven for treating himself and spending his newly-found budget on signing Andreas Weimann from Aston Villa for £3m in 2015.

Mauricio Pochettino

First Tottenham signing: Ben Davies and Michel Vorm (from Swansea for Gylfi Sigurdsson, 2014)
Most expensive career signing: Moussa Sissoko (Newcastle to Tottenham for £30m, 2016)

First career signing: Mauricio Pochettino was tasked with rescuing a seemingly doomed Espanyol side when appointed to his first managerial post in January 2009. He achieved what was thought to be impossible thanks in no small part to his first signing, Ivan Alonso, who scored five goals and assisted two in 16 La Liga games after joining that winter.

Marco Silva

First Watford signing: N/A
Most expensive career signing: Kamil Grosicki (Rennes to Hull for £7m, 2017)

First career signing: Marco Silva relied upon a few familiar faces from his past in his attempt to spare Hull the fate of Premier League relegation. He had managed both Evandro and Omar Elabdellaoui previously, but the only player he ever signed twice was winger Sebá, who he first bought from Cruzeiro for Estoril in 2011.

Tony Pulis

First West Brom signing: Callum McManaman (from Wigan for £4.75m, 2015)
Most expensive career signing: Nacer Chadli (Tottenham to West Brom for £13m, 2016)

First career signing: That Tony Pulis’ first ever signing as a manager, Steve Fletcher, is now a 44-year-old assistant first-team coach at Bournemouth, tells its own story. The becapped Welshman signed Fletcher from Hartlepool for £40,000 in 1992, and the striker would make more than 580 appearances at Dean Court over 15 years. He left in 2007 but returned a few years later, and now holds the record for most Bournemouth appearances. And it all started with Big Tone.

Slaven Bilic

First West Ham signing: Pedro Obiang (from Sampdoria for £5m, 2015)
Most expensive career signing: Andre Ayew (Swansea to West Ham for £20.5m, 2016)

First career signing: Poor Slaven Bilic had to wait ten years between his first and second ever signings as a manager. He enjoyed a brief spell with Hajduk Split in 2001, winning 11 of his 16 games before leaving. He signed just one player there – attacking midfielder Pablo Munhos – before taking over Croatia’s U21 side, then the seniors in 2006. His next club job was with Lokomotiv Moscow in 2012.

Source: http://www.football365.com/news/each-current-pl-managers-first-and-most-expensive-signings