In the days of the Premier League, there were a number of quality free transfer signings in Sol Campbell, Hermann Hreidarsson, Sylvain Distin and Kanu.
Before then were Robert Prosinecki, Paul Merson, Shaka Hislop and Arjan de Zeeuw, among many others.
But how about the outstanding freebies snapped up by the Blues since departing the Premier League in May 2010?
Well, here are our 15 best Pompey free transfer recruits since then, in no particular order...
1. Craig MacGillivray - 135 games, 0 goals
Credit to Kenny Jackett for identifying the talent of Shrewsbury’s number two goalkeeper and bringing him to Fratton Park in June 2018. MacGillivray had produced a man-of-the-match display against the Blues in a rare outing in January 2018, something which lodged in the mind of their manager at the time. During three seasons on the south coast, MacGillivray was a popular performer, cemented by his decisive penalty save in the Checkatrade Trophy final against Sunderland to win it at Wembley. The option on his contract was surprisingly not taken up at the end of the 2020-21 season by Danny Cowley and the goalkeeper departed as The News/Sports Mail’s Player of the Season. | PinPep Media / Joe Pepler
2. Michael Doyle - 97 games, three goals
Doyle actually walked out of Southampton airport ahead of the 2015 pre-season trip to the Algarve when he discovered Pompey could not yet complete a deal to sign him on a free transfer. Still, not long after, the contract he desired was finally tabled and the combative midfielder went on to become a pivotal player in two seasons under Paul Cook. Crowned The News/Sports Mail’s Player of the Season in 2015-16, the following campaign he led the Blues to the League Two title on that dramatic final day against Cheltenham. Within weeks of that glorious moment, he left Fratton Park to sign for Coventry after not being convinced he would receive another Pompey contract, yet his legacy remains intact. | Joe Pepler/Digital South
3. Conor Shaughnessy - 49 games, four goals
Many wrote off the central defender before he even featured for the Blues purely on the basis he arrived from Burton as a free transfer. However, by the campaign’s end Shaughnessy had scored the goal which secured the League One title, while had also deservedly been named in the EFL divisional Team of the Season. Classy on the ball, composed at the back and with a habit of weighing in with crucial late goals, the Irishman was undoubtedly one of the stars of the promotion campaign. Indeed, after being left out of the opening match of the season, he started the remaining 45 fixtures and was named as the Players’ Player Of The Year. | Jason Brown/ProSportsImages
4. Johnny Ertl - 88 games, two goals
Ertl was of a time at Fratton Park, when Pompey were struggling against administration, threatened with liquidation and fighting to remain in the Football League. During such tough days, the Austrian was a whole-hearted performer, passionate, hard-working and fully committed to the Blues cause - on and off the pitch. Indeed, he even bought a share in the Pompey Supporters’ Trust and later sat on their board in post-playing days. The News/Sports Mail’s Player of the Season in 2012-13 played his last match in May 2015 during his Stag weekend, before new boss Paul Cook told him he wasn’t part of his plans. | Joe Pepler/ Colorsport Photo: Joe Pepler