The transfer market for smaller clubs can always be tricky business.
Unlike the big clubs that can splash big cash on proven commodities, smaller clubs often have to take chances on players that are still a bit unproven, coming from different environments in other countries, or looking to regain form after a bout with an injury or lack of first-team action.
Southampton have surely had their hits and misses in the transfer market over the years. Even looking at this past season, you can already see some transfers that were well worth the price (Nathaniel Clyne, £2.86 million from Crystal Palace; Maya Yoshida, £2.46 million from VVV-Venlo) and some that may not (Vegard Forren, £4.18 million from Molde FK).
The infamous Ali Dia signing took place before the scope of this article in 1996, so it won't be included. But that signing didn't cost any money besides a one-month contract. These five signings cost the Saints a good amount of money without much return.
The Five Worst Southampton Signings Since 1998
5. Wayne Thomas (2007, £1.49 million from Burnley)
Wayne Thomas wasn't the worst player Southampton ever signed. The center back made 54 appearances for Southampton over three seasons. It's just that the Saints paid way too much for him. 1.5 million pounds is a lot of money for a Championship-level side that was on the verge of going into administration.
The Englishman has never had a market value of more than £400,000 according to transfermarkt.co.uk. Stoke City only paid £264,000 for Thomas when they acquired him, so Southampton probably could have got him or another player of his caliber for half the price.
Thomas left Southampton after his contract was not renewed in 2010 while the club was still in League One.
4. Neil McCann (2003, £1.95 million from Rangers)
At first, it looked like Southampton might have made a pretty good deal with Rangers to get McCann at just under two million pounds.
But the Scottish international battled injuries throughout his time on the South Coast. When McCann was on the pitch, he didn't have much of an impact. The left-winger failed to score and only provided two assists in his 43 appearances with the Saints.
McCann left the club in 2006 by mutual consent after Southampton had been relegated to the Championship.
3. Mark Draper (2001, £1.98 million from Aston Villa)
The 2001-02 season was actually a decent season transfer wise for Southampton. Three players that would be part of the 2003 FA Cup Final squad, Brett Ormerod, Fabrice Fernandes and Anders Svensson, along with then-club record signing Rory Delap were all brought to the South Coast that season.
One player that got lost in the shuffle was Mark Draper.
Draper would play 22 matches in the 2001-02 season and score one goal, but faded into obscurity soon after. The midfielder would only make two more appearances for the Saints and retired from the game in 2003.
2. Imants Bleidelis (1999, £770,000 from Skonto Riga)
In 1998, Southampton signed a Latvian from Skonto Riga, and that turned out pretty well (see the best list later on for more details).
So in 1999, the Saints tried to go to the well one more time by signing Imants Bleidelis from Skonto. The Latvian midfielder failed to have any impact with the Saints.
Bleidelis only played in two matches for Southampton. Both appearances were as a substitute totaling 10 minutes of action.
Mr. Dia lasted 20 minutes in his infamous appearance, double what Bleidelis contributed to the club over three seasons at Southampton.
1. Jelle van Damme (2004, £2.64 million from AFC Ajax)
The summer of 2004 was a season of turmoil at Southampton. After Gordon Strachan resigned late in the 2003-04 season, he was replaced by somewhat unknown Paul Sturrock of Plymouth Argyle.
Sturrock brought in a cast of characters that wouldn't spend much time at Southampton: Nigel Quashie, Peter Crouch and Andreas Jakobsson among them.
Jelle van Damme was a promising wing back that could also play as a midfielder who was struggling to find playing time at Dutch power Ajax. Sturrock brought him in for over 2.6 million pounds, despite the fact that the young Belgian had only played 18 first-team games at Ajax.
Van Damme never caught on with Saints. Sturrock, and later Steve Wigley and Harry Redknapp, would only give him six appearances and Southampton were relegated that season.
After a season on loan at Werder Bremen, Southampton gave up on the young defender and sold him to Anderlecht for just 440,000 pounds.
Thankfully, Southampton have managed to cash in on a number of bargains over the years to make up for those misses. Three of Southampton's best transfer signings are still on the squad today.
The Five Best Southampton Signings Since 1998
5. Kelvin Davis (2006, £990,000 from Sunderland)
While Kelvin Davis may not be a key part of the current Southampton squad, the Saints wouldn't be where they are now without him.
Brought in from Sunderland for just under a million pounds while Saints were in the Championship, Davis has been a loyal servant for the club. The veteran keeper stayed with Southampton through administration and relegation to League One despite opportunities to leave, and was a constant in the squads that climbed the ladder back to the Premier League.
Davis has made 279 appearances for the club over the past six seasons. Pretty good value for a million pounds.
4. Marian Pahars (1999, £1.05 million from Skonto Riga)
If Marian Pahars only played the one match against Everton on May 16, 1999, he still would have been worth the transfer fee.
The "Little Latvian" scored both goals in a 2-0 victory that capped Southampton's "Great Escape," which kept the Saints in the Premier League and provided the momentum needed to build St. Mary's Stadium to replace The Dell.
Pahars did more than that in his Southampton career of course. The Latvian made 138 appearances for the Saints, scoring 43 goals and becoming a club cult legend in the process.
3. Morgan Schneiderlin (2008, £1.32 million from Strasbourg)
Schneiderlin joined the Saints in 2008 right before the club would go into administration, as the club was forced to field a young, untested side.
Strangely, the relegation to League One may have been a good thing for Schneiderlin, as he could receive playing time while he matured and his skills improved.
After just one season in the Premier League, the Frenchman is considered one of the best defensive midfielders in the league. Schneiderlin ranked first in interceptions and second in tackles in the Premier League according to WhoScored.com.
If Southampton do decide to sell Schneiderlin for some reason, at least the Saints will make a nice profit. The rumored price tag for the midfielder is 10 million pounds.
Pahars wasn't the only talented striker to join Southampton during the 1998-99 season. James Beattie came to the South Coast in the summer of 1998 to help take the place of aging legend Matt Le Tissier.
It's never easy to follow a legend, but Beattie did quite well in his time at Southampton. The English native played 204 matches for the Saints, and scored 68 times.
Beattie would move on in January 2005 as Southampton were in managerial chaos en route to relegation. But the Saints would make a nice profit on the deal, as Everton would pay £7.92 million to bring the striker to Goodison Park.
1. Rickie Lambert (2009, £1.05 million from Bristol Rovers)
Considering the millions and millions of pounds that are at stake in the Premier League, £10,000 per goal scored might be one of the biggest steals in Premier League history.
One million pounds isn't cheap for a team in League One, as Southampton was when they bought the journeyman striker. But Lambert was part of the initial spending spree in Markus Liebherr's first season as owner and Nicola Cortese's first season as chairman. That spree also included Jose Fonte and Jason Puncheon.
"Southampton's Goal Machine" has been worth at least three times his transfer fee, as Lambert has scored 100 goals in just 189 matches with Southampton. His 15 goals were tied for the most of any English player (with Frank Lampard) in the Premier League.
All transfer fees according to transfermarkt.co.uk