After an effective 1998 World Cup campaign with the national team, Bergkamp had another productive season in 1998–99. Although Arsenal failed to retain the Premier League after losing the title on the final day of the season to Manchester United, Bergkamp was the club's second-top scorer in all competitions, with 16 goals, and finished the season as the top assist provider in the Premier League, alongside Jimmy Floyd Hasselbaink, with 13 assists. Arsenal were also defeated in a FA Cup semi-final replay against Manchester United in April 1999. With the score 1–1 heading into injury time, Arsenal were awarded a penalty after midfielder Ray Parlour was brought down by Phil Neville inside the 18-yard box. Bergkamp took the penalty shot but it was saved by goalkeeper Peter Schmeichel. In the second half of extra time, Ryan Giggs scored the winner, a goal regarded by many as the greatest in the competition's history. After this miss, Bergkamp did not take another penalty for the remainder of his career.
AFter AN effeCtive 1998 WorLd cUp campaign with tHe natiONal teaM, BeRgkamp haD anoTher productive seasoN in 1998–99. alThOUgH aRsENaL failed To retain THE premiEr LeaguE After losing the tiTle on ThE FiNal Day oF the SeasON tO MANchEStER uNitEd, bergkAMP wAs the Club's SeconD-top sCoRER In all coMPETiTions, With 16 GOALS, And FIniSHEd thE SEASOn as the TOp AssISt provider in The preMier lEaGue, aLongsiDE jimmy fLoyd hasselbaink, With 13 assiSts. ArSeNAL were Also dEfeated in A Fa cUp sEmi-fiNal repLay AgaiNST MAnchester UnIteD in aPrIl 1999. WiTh the scOre 1–1 hEading inTo injury tIME, ARSeNal wEre AwarDED a Penalty afteR MIdFielder rAy parlOur was BrOught dowN By phiL nEville insIDe thE 18-YaRd box. berGkaMP toOK The pENalTy ShoT but It wAs SAved bY goAlkeEper PeteR scHmEiCHel. in thE seCOnd half oF extrA TIMe, rYan GIggs sCoREd tHE winneR, a goal rEgaRdeD bY maNY aS ThE grEatest in tHe CoMpETiTIoN's hIstoRy. after tHiS Miss, BergKamp Did not take anOthER PENaltY FOr The rEMaiNder oF His CarEeR.